methyl 2,3,3aβ,4,5,7aα-hexahydroindene-4β-carboxylate | 80595-29-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,3aβ,4,5,7aα-hexahydroindene-4β-carboxylate
• 英文别名: methyl (3aR,4R,7aS)-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylate
• CAS: 80595-29-5
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: DRCBJOYOGDOCNF-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2,3,3aβ,4,5,7aα-hexahydroindene-4β-carboxylate 生成 2,3,3aβ,4,5,7aα-hexahydroindene-4β-carboxylic acid
  参考文献：
  名称：

  Stereochemical aspects of the intramolecular Diels-Alder reactions of methyl deca-2,7,9-trienoates. 1. Thermal cyclizations

  摘要：

  DOI：

  10.1021/jo01309a054
• 作为产物：
  描述：

  (E)-7-氧代庚-2-烯酸甲酯 生成 methyl 2,3,3aβ,4,5,7aα-hexahydroindene-4β-carboxylate
  参考文献：
  名称：

  A Study of the Intramolecular Diels-Alder Reaction¹

  摘要：

  DOI：

  10.1021/jo01015a026

文献信息

• Liquid crystal control. A remarkable enhancement of both efficiency and diastereoselectivity of intramolecular thermal cycloadditions in smectic solvents
  作者：Kenji Fukunaga、Takehisa Kunieda

  DOI：10.1016/s0040-4039(99)01200-9

  日期：1999.8

  The uncatalyzed intramolecular [4+2]cycloaddition of 2E, 7E,9(E)-decatrienoates, conducted at 140 °C in a medium of smectic liquid cryctals proceeds with a remarkably high level of chemical efficiency and diastereselectivity, in contrast to the isotropic phase reactions which result in much lower yield and selectivity.

  与近晶相液体相反，在近层液态结晶介质中于140°C进行的2 E，7 E，9（E）-十碳三烯酸酯的未催化分子内[4 + 2]环加成反应具有很高的化学效率和非对映选择性。各向同性的相反应会大大降低收率和选择性。
• Stereochemical aspects of the intramolecular Diels-Alder reactions of deca-2,7,9-trienoate esters. 3. Thermal, Lewis acid catalyzed, and asymmetric cyclizations
  作者：William R. Roush、Herbert R. Gillis、Albert I. Ko

  DOI：10.1021/ja00372a027

  日期：1982.4
• Stereochemical control in intramolecular Diels-Alder reactions with carbene complexes as ester synthons
  作者：William D. Wulff、Timothy S. Powers

  DOI：10.1021/jo00061a008

  日期：1993.4

  An evaluation of the intramolecular Diels-Alder reactions of Fischer carbene complexes was made for complexes which have an all-carbon tether between the diene and dienophile. Specifically, both the cis- and trans-isomers of the deca-2,7,9-trienyl carbene complexes (26-cis, 24-trans) and the undeca-2,8,10-trienyl carbene complexes (27-cis, 25-trans) were prepared and the rates and stereoselectivities of their intramolecular Diels-Alder reactions were in each case compared with those of the known reactions of their corresponding methyl esters. For the deca-2,7,9-trienyl complexes 24 and 26, the stereoselectivities are comparable to those observed for the Lewis-acid-catalyzed reactions of their corresponding methyl esters and much higher than the thermal reactions of the methyl esters which are completely unselective. The undeca-2,8,10-trienyl complex 25 undergoes intramolecular Diels-Alder reaction with a 93:7 endo/exo selectivity whereas the corresponding methyl ester 7 is known to give a 51:49 selectivity under thermal conditions and to fail with attempts at Lewis acid catalysis. The cis-substituted complex 27 also undergoes a selective reaction where the corresponding reaction of the ester fails. In addition no trace of isomerization of the cis-complex 27 could be observed during its cycloaddition. The triphenylphosphine and isopropoxy complexes 28-30 were prepared, and the stereoselectivity of their intramolecular Diels-Alder reactions is consistent with an s-trans conformation of the vinyl carbene funtionality in the transition state. In all cases the carbene complex cycloadducts can be oxidatively cleaved in high yield to their corresponding esters. The results show that the value of these complexes as synthons for esters is a result of tolerance of the carbene complex functional group to sensitive diene units which do not tolerate traditional Lewis acids utilized in accelerating intramolecular Diels-Alder reactions.
• Stereochemical aspects of the intramolecular Diels-Alder reactions of methyl deca-2,7,9-trienoates. 2. Lewis acid catalysis
  作者：William R. Roush、Herbert R. Gillis

  DOI：10.1021/jo01309a055

  日期：1980.10
• ROUSH R. W.; KO A. I.; GILLIS H. R., J. ORG. CHEM., 1980, 45, NO 21, 4264-4267
  作者：ROUSH R. W.、 KO A. I.、 GILLIS H. R.

  DOI：——

  日期：——