(E)-8-(tert-butyldimethylsilyloxy)-8-(furan-2-yl)-oct-5-enoic acid | 1415237-44-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-8-(tert-butyldimethylsilyloxy)-8-(furan-2-yl)-oct-5-enoic acid
• 英文别名: (E)-8-[tert-butyl(dimethyl)silyl]oxy-8-(furan-2-yl)oct-5-enoic acid
• CAS: 1415237-44-3
• 化学式: C₁₈H₃₀O₄Si
• 分子量: 338.519
• InChiKey: NBNYYWIWVPSECO-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-碘代丙烷 、 (E)-8-(tert-butyldimethylsilyloxy)-8-(furan-2-yl)-oct-5-enoic acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 isopropyl (E)-8-(tert-butyldimethylsilyloxy)-8-(furan-2-yl)-oct-5-enoate
  参考文献：
  名称：

  合成前列腺素类似物的手性4-甲硅烷基环戊烯酮中间体的制备

  摘要：

  A process is described for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural. Key steps in the synthesis include a Wittig reaction, Piancatelli rearrangement, and an enzymatic resolution featuring in situ

  DOI：

  10.1021/op300188x
• 作为产物：
  描述：

  5-溴戊酸 在 三(N,N-四亚甲基)磷酰胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.4h， 生成 (E)-8-(tert-butyldimethylsilyloxy)-8-(furan-2-yl)-oct-5-enoic acid
  参考文献：
  名称：

  合成前列腺素类似物的手性4-甲硅烷基环戊烯酮中间体的制备

  摘要：

  A process is described for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural. Key steps in the synthesis include a Wittig reaction, Piancatelli rearrangement, and an enzymatic resolution featuring in situ

  DOI：

  10.1021/op300188x

文献信息

• Process for the Preparation of Prostaglandin Analogues and Intermediates Thereof
  申请人：Henschke Julian P.

  公开号：US20090259058A1

  公开（公告）日：2009-10-15

  The present application provides intermediates for preparing prostaglandin analogues and processes for preparing prostaglandin analogues and intermediates thereof. The intermediates include: A compound of formula (6): R 1 represents H, C 1 -C 5 -alkyl, or benzyl, in particular isopropyl.

  本申请提供了用于制备前列腺素类似物的中间体以及制备前列腺素类似物和其中间体的方法。这些中间体包括：化合物的公式（6）： R 1 代表H，C 1 -C 5 -烷基，或苄基，特别是异丙基。
• The Manufacture of a Homochiral 4-Silyloxycyclopentenone Intermediate for the Synthesis of Prostaglandin Analogues
  作者：Julian P. Henschke、Yuanlian Liu、Xiaohong Huang、Yungfa Chen、Dechao Meng、Lizhen Xia、Xiuqiong Wei、Aiping Xie、Danhong Li、Qiang Huang、Ting Sun、Juan Wang、Xuebin Gu、Xinyan Huang、Longhu Wang、Jun Xiao、Shenhai Qiu

  DOI：10.1021/op300188x

  日期：2012.12.21

  A process is described for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural. Key steps in the synthesis include a Wittig reaction, Piancatelli rearrangement, and an enzymatic resolution featuring in situ

  A process is described for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural. Key steps in the synthesis include a Wittig reaction, Piancatelli rearrangement, and an enzymatic resolution featuring in situ