(E)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptenoate | 171598-87-1

• 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: (E)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptenoate
• 英文别名: methyl 2-[(4R,6S)-2,2-dimethyl-6-[(E)-2-phenylethenyl]-1,3-dioxan-4-yl]acetate
• CAS: 171598-87-1
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: IOBOLJSHLCWRQV-SXKCSBRWSA-N

物化性质

• 沸点：
  383.5±27.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptenoate 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以75%的产率得到瑞舒伐他汀杂质121
  参考文献：
  名称：

  Short and efficient chemoenzymatic synthesis of goniothalamin

  摘要：

  A high-yielding three-step synthesis of goniothalamin involving an enzymatic kinetic resolution in the presence of vinyl acrylate followed by ring-closing metathesis is discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.115
• 作为产物：
  描述：

  (1R,4S,6R)-4-((E)-Styryl)-3,7-dioxa-bicyclo[4.1.0]heptan-2-one 在 sodium tetrahydroborate 、 二苯基二硒醚 、 对甲苯磺酸 、 copper(II) sulfate 作用下， 生成 (E)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptenoate
  参考文献：
  名称：

  Short and efficient chemoenzymatic synthesis of goniothalamin

  摘要：

  A high-yielding three-step synthesis of goniothalamin involving an enzymatic kinetic resolution in the presence of vinyl acrylate followed by ring-closing metathesis is discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.115

文献信息

• Chiral Sulfoxides in Asymmetric Synthesis: Enantioselective Synthesis of the Lactonic Moiety of (+)-Compactin and (+)-Mevinolin. Application to a Compactin Analog
  作者：Guy Solladie、Claude Bauder、Leucio Rossi

  DOI：10.1021/jo00129a018

  日期：1995.12

  The lactonic part of (+)-compactin and (+)-mevinolin as well as a compactin analogue were synthesized in an enantioselective way from a beta,delta-diketo sulfoxide easily obtained by the reaction of the trianion of methyl 3,5-dioxohexanoate with (-)-menthyl (S)-p-toluenesulfinate. The main reaction was the two-step stereoselective reduction of beta,delta-diketo sulfoxide without any protective group.
• Short and efficient chemoenzymatic synthesis of goniothalamin
  作者：Michelangelo Gruttadauria、Paolo Lo Meo、Renato Noto

  DOI：10.1016/j.tetlet.2003.10.115

  日期：2004.1

  A high-yielding three-step synthesis of goniothalamin involving an enzymatic kinetic resolution in the presence of vinyl acrylate followed by ring-closing metathesis is discussed. (C) 2003 Elsevier Ltd. All rights reserved.