isopropyl E-5-hydroxy-3-oxo-6-octenoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: isopropyl E-5-hydroxy-3-oxo-6-octenoate
• 英文别名: propan-2-yl (E)-5-hydroxy-3-oxooct-6-enoate
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: JFYGRLCBGRMTMW-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl E-5-hydroxy-3-oxo-6-octenoate 在 L-Selectride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 (E)-Isopropyl 2-methyl-4-oxo-6-(prop-1-enyl)tetrahydro-2H-pyran-3-carboxylate
  参考文献：
  名称：

  A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones

  摘要：

  已开发出新的Maitland–Japp反应变体，可用于合成带有三级和四级立体中心的二氢吡喃和四氢吡喃，包括Civet中的官能化四氢吡喃和lasonolide A的A环。

  DOI：

  10.1039/c5ob00292c

文献信息

• Process for preparation of 5-hydroxy-3-ketoester derivative and optically active substance thereof
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0641762A1

  公开（公告）日：1995-03-08

  Disclosed is a process for the preparation of a 5-hydroxy-3-ketoester derivative of the formula: in which R¹ represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, and R² represents an alkyl group or an aryl group, which comprises causing the reaction of an aldehyde compound of the formula R¹CHO in which R¹ has the meanings as defined above and diketene in the presence of a metal compound selected from a titanium or aluminum compound having at least one group of -OR³ in which R³ represents an alkyl group or an aryl group. Further, a process for the preparation of an optically active substance of the 5-hydroxy-3-ketoester derivative causing the reaction of the above compounds in the presence of the metal compound and optically active Schiff base or a complex compound obtained by reacting the metal compound with the optically active Schiff base, also is disclosed.

  本发明公开了一种制备式 5-羟基-3-酮酯衍生物的工艺： 其中R¹代表烷基、烯基、炔基、芳基或杂环基，R²代表烷基或芳基，其包括使式R¹CHO的醛化合物（其中R¹具有如上定义的含义）和二乙烯在选自钛或铝化合物的金属化合物存在下反应，该金属化合物具有至少一个-OR³基团，其中R³代表烷基或芳基。此外，本发明还公开了一种制备 5-羟基-3-酮酯衍生物的光学活性物质的工艺，该工艺使上述化合物在金属化合物和光学活性席夫碱或金属化合物与光学活性席夫碱反应得到的复合物的存在下发生反应。
• US5457225A
  申请人：——

  公开号：US5457225A

  公开（公告）日：1995-10-10
• A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones
  作者：Paul A. Clarke、Philip B. Sellars、Nadiah Mad Nasir

  DOI：10.1039/c5ob00292c

  日期：——

  New variations of the Maitland–Japp reaction have been developed to enable the synthesis of dihydropyrans and tetrahydropyrans with tertiary and quaternary stereocentres, including the functionalised tetrahydropyrans in Civet and the A-ring of lasonolide A.

  已开发出新的Maitland–Japp反应变体，可用于合成带有三级和四级立体中心的二氢吡喃和四氢吡喃，包括Civet中的官能化四氢吡喃和lasonolide A的A环。