FORMATION OF METHYL 11-HYDROXY-8-OXOPENTACYCLO[5.4.0.0(2,6).0(3,10).0(5,9)]UNDECANECARBOXYLATE BY A REGIOSPECIFIC AND STEREOSPECIFIC REDUCTION

被引：3

作者：

WATSON, WH ^{[1
]}

KASHYAP, RP ^{[1
]}

MARCHAND, AP ^{[1
]}

REDDY, SP ^{[1
]}

机构：

[1] UNIV N TEXAS,DEPT CHEM,DENTON,TX 76203

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS | 1991年 / 47卷

关键词：

D O I：

10.1107/S0108270190005406

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methyl 11-hydroxy-8-oxopentacyclo-[5.4.0.0(2,6).0(3,10).0(5, 9]undecanecarboxylate (3), C13H14-O4, M(r) = 234.26, triclinic, P1BAR, a = 7.291 (1), b = 7.441 (1), c = 10.414 (1) angstrom, alpha = 104.56 (1), beta = 90.41 (1), gamma = 99.07 (1)-degrees, V = 539.3 (1) angstrom 3, Z = 2, D(x) = 1.442 g cm-3, lambda-(Mo K-alpha) = 0.71073 angstrom, mu = 1.00 cm-1, F(000) = 248, T = 295 K, R = 0.0487 for 2138 reflections. Compound (3) contains four five-membered rings and a four-membered ring fused to form an open-ended cage structure. The through-bond interaction of the pi-systems in the parent diketone is absent in compound (3), which is reflected in the reduction of bond lengths. Although one C-C bond is 1.579 (2) angstrom, it has been shortened significantly. A hydrogen bond is formed between the hydroxyl group and the carbonyl O atom of the ester.

引用

收藏

页码：376 / 378

页数：3

相关论文

共 13 条

[1] 1,6-DIMETHYL-1-ALPHA,4-ALPHA,4A-ALPHA,5-ALPHA,8-BETA,8A-ALPHA-HEXAHYDRO-1,4-METHANONAPHTHALENE-5,8-DIOL [J].

FLIPPENANDERSON, JL ;

GILARDI, R ;

GEORGE, C ;

MARCHAND, AP ;

JIN, PW .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 :2151-2153

[2] REDUCTION OF NATURAL ENONES IN PRESENCE OF CERIUM TRICHLORIDE [J].

LUCHE, JL ;

RODRIGUEZHAHN, L ;

CRABBE, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (14) :601-602

[3]

Marchand A.P., 1989, ADV THEORETICALLY IN, P357

[4] SYNTHESIS OF ALKENE-SUBSTITUTED PENTACYCLO[5.4.0.0/2.6/0/3.10/0/5.9]UNDECANES .2. PHOTOELECTRON-SPECTRA AND ELECTRONIC-STRUCTURES OF SUBSTITUTED PENTACYCLO[5.4.0.0/2.6/0/3.10/0/5.9]UNDECANES [J].

MARCHAND, AP ;

HUANG, C ;

KAYA, R ;

BAKER, AD ;

JEMMIS, ED ;

DIXON, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7095-7101

[5] SYNTHESIS OF METHYL-SUBSTITUTED AND NITRO-SUBSTITUTED PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECANE-8,11-DIONES [J].

MARCHAND, AP ;

SURI, SC ;

EARLYWINE, AD ;

POWELL, DR ;

VANDERHELM, D .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (04) :670-675

[6] FACILE STEREOSELECTIVE REDUCTIONS OF ENEDIONES AND CAGE DIKETONES USING NABH4-CECL3 [J].

MARCHAND, AP ;

LAROE, WD ;

SHARMA, GVM ;

SURI, SC ;

REDDY, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1622-1625

[7]

OSAWA E, 1986, MOL STRUCTURE ENERGE, V3, P355

[8] PRESSURE EFFECT ON THE PRODUCT DISTRIBUTION IN COMPETING REACTIONS - FORMATION OF A BIS DIELS-ALDER ADDUCT VIA AN AROMATIZABLE INTERMEDIATE [J].

SRIVASTAVA, S ;

MARCHAND, AP ;

VIDYASAGAR, V ;

FLIPPENANDERSON, JL ;

GILARDI, R ;

GEORGE, C ;

ZACHWIEJA, Z ;

LENOBLE, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :247-249

[9] STRUCTURE OF A PENTACYCLIC CAGE ENONE [J].

WATSON, WH ;

KASHYAP, RP ;

MARCHAND, AP ;

VIDYASAGAR, V .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1990, 46 :926-928

[10] REGIOSPECIFIC FORMATION OF A METHYL PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECANE-8,11-DIONE-9-CARBOXYLATE MONOKETAL [J].

WATSON, WH ;

NAGL, A ;

MARCHAND, AP ;

REDDY, GM ;

REDDY, SP .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :659-661