(R)-4-(methoxymethoxy)hex-5-enoic acid | 1224601-76-6

• 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: (R)-4-(methoxymethoxy)hex-5-enoic acid
• 英文别名: (4R)-4-(methoxymethoxy)hex-5-enoic acid
• CAS: 1224601-76-6
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: ZKVCCHAJLPHYRL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-(methoxymethoxy)hex-5-enoic acid 、 (R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl]butan-1-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到[(1R)-1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]butyl] (4R)-4-(methoxymethoxy)hex-5-enoate
  参考文献：
  名称：

  Total synthesis of the phytotoxic stagonolides A and B

  摘要：

  The chemo-enzymatic and covergent synthesis of stagonolide B and the synthesis of stagonolide A, a phytotoxic 10-membered lactone have been achieved starting from D-ribose with overall yields of 25% and 8.7%, respectively. The synthesis contained simple steps in developing three centers' key intermediates, namely the enzymatic (Novozyme-435) resolution of a propargylic alcohol followed by macrolactonization and RCM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.010
• 作为产物：
  描述：

  (R)-4-(methoxymethoxy)hex-5-enal 在 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 以95%的产率得到(R)-4-(methoxymethoxy)hex-5-enoic acid
  参考文献：
  名称：

  Total synthesis of the phytotoxic stagonolides A and B

  摘要：

  The chemo-enzymatic and covergent synthesis of stagonolide B and the synthesis of stagonolide A, a phytotoxic 10-membered lactone have been achieved starting from D-ribose with overall yields of 25% and 8.7%, respectively. The synthesis contained simple steps in developing three centers' key intermediates, namely the enzymatic (Novozyme-435) resolution of a propargylic alcohol followed by macrolactonization and RCM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.010

文献信息

• ORGANOCATALYTIC PROCESS FOR ASYMMETRIC SYNTHESIS OF DECANOLIDES
  申请人：Council of Scientific and Industrial Research

  公开号：US20160272609A1

  公开（公告）日：2016-09-22

  The present invention discloses organocatalytic process for asymmetric synthesis of highly enantioselective decanolide compounds in high yield with >99% ee. Further, the present invention disclose cost effective, improved organocatalytic process for asymmetric synthesis of highly enantioselective decanolides compounds from non-chiral, cheap, easily available raw materials.

  本发明揭示了一种有机催化过程，用于高产率地不对称合成高对映选择性的十内酯化合物，其对映体纯度>99%。此外，本发明还揭示了一种成本效益高、改进的有机催化过程，用于从非手性、廉价、易得原料合成高对映选择性的十内酯化合物。
• US9809566B2
  申请人：——

  公开号：US9809566B2

  公开（公告）日：2017-11-07
• Total synthesis of the phytotoxic stagonolides A and B
  作者：Peddikotla Prabhakar、Singanaboina Rajaram、Dorigondla Kumar Reddy、Vanam Shekar、Yenamandra Venkateswarlu

  DOI：10.1016/j.tetasy.2010.01.010

  日期：2010.2

  The chemo-enzymatic and covergent synthesis of stagonolide B and the synthesis of stagonolide A, a phytotoxic 10-membered lactone have been achieved starting from D-ribose with overall yields of 25% and 8.7%, respectively. The synthesis contained simple steps in developing three centers' key intermediates, namely the enzymatic (Novozyme-435) resolution of a propargylic alcohol followed by macrolactonization and RCM. (C) 2010 Elsevier Ltd. All rights reserved.