(+/-)-methyl (3aS,6R,7S,7aR)-6-benzoyloxy-1-oxo-3,3a,6,7,7a-hexahydro-7-isobenzofuran-carboxylate | 114132-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-methyl (3aS,6R,7S,7aR)-6-benzoyloxy-1-oxo-3,3a,6,7,7a-hexahydro-7-isobenzofuran-carboxylate
• 英文别名: (3aα,4α,5α,7aβ)-5-(benzoyloxy)-1,3,3a,4,5,7a-hexahydro-3-oxo-4-isobenzofurancarboxylic acid methyl ester；methyl (3aR,4S,5R,7aS)-5-benzoyloxy-3-oxo-3a,4,5,7a-tetrahydro-1H-2-benzofuran-4-carboxylate
• CAS: 114132-98-8；114133-11-8
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: BPQSJQFQNHRFPW-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  methyl (E)-4-chloro-4-oxo-2-butenoate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (+/-)-methyl (3aS,6R,7S,7aR)-6-benzoyloxy-1-oxo-3,3a,6,7,7a-hexahydro-7-isobenzofuran-carboxylate
  参考文献：
  名称：

  用CBAD方法处理油菜素类固醇；从吡啶获得C环前体

  摘要：

  戊二醛的钾盐（一种吡啶的降解产物）已通过IMDA环化（二甲基富马酸酯）和贝克的酵母介导的酮酸酯还原而转化为光学活性的2,3,4-三取代的环己酮立体化学模式与标题化合物中C环显示的模式密切相关。

  DOI：

  10.1016/s0040-4039(00)76707-4

文献信息

• A C-B-A-D approach to brassinosteroids; obtention of a C-ring precursor from pyridine
  作者：L. Berthon、A. Tahri、D. Uguen

  DOI：10.1016/s0040-4039(00)76707-4

  日期：1994.6

  The potassium salt of glutaconaldehyde, a degradation product of pyridine, has been converted, via inter alia IMDA cyclisation of a dienyl fumaric ester and baker's yeast-mediated reduction of a ketoester, into an optically-active 2,3,4-trisubstituted cyclohexanone having a stereochemical pattern strongly related to that displayed by the C-ring in the title compounds.

  戊二醛的钾盐（一种吡啶的降解产物）已通过IMDA环化（二甲基富马酸酯）和贝克的酵母介导的酮酸酯还原而转化为光学活性的2,3,4-三取代的环己酮立体化学模式与标题化合物中C环显示的模式密切相关。
• Intra- and intermolecular Diels-Alder reactions of glutaconaldehyde derivatives
  作者：Jan Becher、Helle Chris Nielsen、Jens Peter Jacobsen、Ole Simonsen、Helen Clausen

  DOI：10.1021/jo00244a005

  日期：1988.4
• BECHER, JAN;NIELSEN, HELLE CHRIS;JACOBSEN, JENS PETER;SIMONSEN, OLE;CLAUS+, J. ORG. CHEM., 53,(1988) N 9, 1862-1871
  作者：BECHER, JAN、NIELSEN, HELLE CHRIS、JACOBSEN, JENS PETER、SIMONSEN, OLE、CLAUS+

  DOI：——

  日期：——
• Intramolecular Diels−Alder Reactions of Ester-Linked 1,3,8-Nonatrienes
  作者：Tory N. Cayzer、Michael N. Paddon-Row、Damian Moran、Alan D. Payne、Michael S. Sherburn、Peter Turner

  DOI：10.1021/jo0505829

  日期：2005.7.1

  Penta-1,3-dienyl acrylates undergo kinetically controlled intramolecular Diels-Alder (lMDA) reactions and DFT calculations (B3LYP/6-31+G(d)) predict stereoselectivities that are in very good agreement with the experimental values. The nature of the diene Cl substituent has virtually no influence upon reactivity or trans/cis-stereoselectivity whereas terminal C9 dienophile substituents have a substantial effect on both the reactivity and stereoselectivity of these IMDA reactions. The TSs highlight contributions from strain in the developing tether-containing ring, and steric and electronic effects between tether and dienophile substituents, thus providing insight into the origins of IMDA reactivity and stereoselectivity.