isopropyl 5-cyclohexyl-5-hydroxy-3-oxopentanoate

• 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 5-cyclohexyl-5-hydroxy-3-oxopentanoate
• 英文别名: Propan-2-yl 5-cyclohexyl-5-hydroxy-3-oxopentanoate
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: QDPKTURCMVMNAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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 5-cyclohexyl-5-hydroxy-3-oxopentanoate 、 1,1-二甲氧基-N,N-二甲基乙胺 以 甲苯 为溶剂， 以81%的产率得到isopropyl 6-cyclohexyl-2-methyl-4-oxo-5,6-dihydro-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
• 作为产物：
  描述：

  环己烷基甲醛 以92%的产率得到isopropyl 5-cyclohexyl-5-hydroxy-3-oxopentanoate
  参考文献：
  名称：

  Process for preparation of 5-hydroxy-3-ketoester derivative and

  摘要：

  披露了一种制备5-羟基-3-酮酯衍生物的工艺，该衍生物的公式为：##STR1##，其中R.sup.1代表烷基、烯基、炔基、芳基或杂环基，R.sup.2代表烷基或芳基，该工艺包括使上述定义的R.sup.1的甲醛化合物R.sup.1 CHO与二酮烯在至少含有一个--OR.sup.3基团的钛或铝化合物存在下发生反应，其中R.sup.3代表烷基或芳基。另外，还披露了一种在金属化合物和光学活性Schiff碱或通过金属化合物与光学活性Schiff碱反应得到的配合物存在下，通过使上述化合物发生反应来制备5-羟基-3-酮酯衍生物的光学活性物质的工艺。

  公开号：

  US05457225A1

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。
• Diastereoselective synthesis of functionalized 2-methyltetrahydropyran-4-ones
  作者：Paul A. Clarke、Philip B. Sellars、Nimesh Mistry

  DOI：10.1016/j.tetlet.2011.05.022

  日期：2011.7

  A simple procedure for the synthesis of functionalized 2-methyl-2,3-dihydropyran-4-ones, based on the Maitland-Japp reaction, and their diastereoselective conversion into functionalized 2-methyltetrahydropyran-4-ones has been developed. This allows access to a structural unit present in a large number of biologically active natural products, and has been successfully applied to the synthesis of the molecule found in Civet cat secretion. (C) 2011 Elsevier Ltd. All rights reserved.
• US5457225A
  申请人：——

  公开号：US5457225A

  公开（公告）日：1995-10-10
• Process for preparation of 5-hydroxy-3-ketoester derivative and
  申请人：Ube Industries Ltd.

  公开号：US05457225A1

  公开（公告）日：1995-10-10

  Disclosed is a process for the preparation of a 5-hydroxy-3-ketoester derivative of the formula: ##STR1## in which R.sup.1 represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, and R.sup.2 represents an alkyl group or an aryl group, which comprises causing the reaction of an aldehyde compound of the formula R.sup.1 CHO in which R.sup.1 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 --OR.sup.3 in which R.sup.3 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.

  披露了一种制备5-羟基-3-酮酯衍生物的工艺，该衍生物的公式为：##STR1##，其中R.sup.1代表烷基、烯基、炔基、芳基或杂环基，R.sup.2代表烷基或芳基，该工艺包括使上述定义的R.sup.1的甲醛化合物R.sup.1 CHO与二酮烯在至少含有一个--OR.sup.3基团的钛或铝化合物存在下发生反应，其中R.sup.3代表烷基或芳基。另外，还披露了一种在金属化合物和光学活性Schiff碱或通过金属化合物与光学活性Schiff碱反应得到的配合物存在下，通过使上述化合物发生反应来制备5-羟基-3-酮酯衍生物的光学活性物质的工艺。
• 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。