3-(tert-butyldimethylsilyloxy)-3-(furan-2-yl)propanal | 1190883-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(tert-butyldimethylsilyloxy)-3-(furan-2-yl)propanal
• 英文别名: 3-(tert-butyldimethylsilyloxy)-3-(furan-2-yl)-propanal；3-[tert-butyl(dimethyl)silyl]oxy-3-(furan-2-yl)propanal
• CAS: 1190883-07-8
• 化学式: C₁₃H₂₂O₃Si
• 分子量: 254.401
• InChiKey: LHSAVEPWENWQCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsilyloxy)-3-(furan-2-yl)propanal 在 三(N,N-四亚甲基)磷酰胺 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 potassium carbonate 、 对苯二酚 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 27.4h， 生成 isopropyl (Z)-7-(3-hydroxy-5-oxo-cyclopent-1-en-1-yl)-hept-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：

  4-(tert-butyldimethylsilyloxy)-4-(furan-2-yl)-butane-1,2-diol 在 sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 反应 33.0h， 以17.8 kg的产率得到3-(tert-butyldimethylsilyloxy)-3-(furan-2-yl)propanal
  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。
• [EN] PROCESS FOR THE PREPARATION OF PROSTAGLANDIN ANALOGUES AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ANALOGUES DE LA PROSTAGLANDINE ET DE LEURS INTERMÉDIAIRES
  申请人：SCINOPHARM TAIWAN LTD

  公开号：WO2009141718A2

  公开（公告）日：2009-11-26

  [00110] 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) Ri represents H, C1-C5-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过程。中间体包括：式（6）的化合物。其中Ri代表H、C1-C5-烷基或苄基，特别是异丙基。
• Process for the preparation of prostaglandin analogues
  申请人：ScinoPharm Taiwan, Ltd.

  公开号：US08742143B2

  公开（公告）日：2014-06-03

  A process for preparing a prostaglandin analogue comprising a step of converting a compound of formula (8′): to the prostaglandin analogue, wherein R3 represents hydrogen or a hydroxyl protecting group.

  一种制备前列腺素类似物的过程，包括将式(8')的化合物转化为前列腺素类似物的步骤，其中R3代表氢或羟基保护基。
• 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