isopropyl 5-hydroxy-3-oxo-5-phenylpentanoate

• 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-hydroxy-3-oxo-5-phenylpentanoate
• 英文别名: isopropyl 5-hydroxy-5-phenyl-3-oxopropanoate；propan-2-yl 5-hydroxy-3-oxo-5-phenylpentanoate
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: KZZKGALMOUVSQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-hydroxy-3-oxo-5-phenylpentanoate 在 L-Selectride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 isopropyl 2-methyl-4-oxo-6-phenyl 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
• 作为产物：
  描述：

  (S)-2-N-(salicylideneamino)-3-methyl-butan-1-ol 以23%的产率得到isopropyl 5-hydroxy-3-oxo-5-phenylpentanoate
  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

• Asymmetric carboncarbon bond forming reactions catalyzed by chiral Schiff base—titanium alkoxide complexes
  作者：Masahiko Hayashi、Tetsuya Inoue、Yasunori Miyamoto、Nobuki Oguni

  DOI：10.1016/s0040-4020(01)89374-1

  日期：1994.4

  The enantioselective addition of trimethylsilyl cyanide to a variety of aldehydes proceeded by the aid of a catalyst prepared in situ from titanium tetraisopropoxide [Ti(O-i-Pr)4] and chiral Schiff bases and gave the corresponding cyanohydrins in high optical yield (up to 96% e.e.). A remarkable rate enhancement was brought about by the addition of the Schiff base to the titanium alkoxide mediated

  在由四异丙醇钛[Ti（O- i- Pr）4 ]和手性席夫碱原位制备的催化剂的帮助下，将三甲基甲硅烷基氰化物对映选择性加成到各种醛中，从而以高光学收率得到了相应的氰醇（最多到96％ee）。通过将席夫碱加入到钛醇盐介导的醛的甲硅烷基氰化中，可以显着提高速率。该催化剂体系还促进了双烯酮与醛的高度对映选择性反应，这导致形成光学活性的5-羟基-3-氧代酯。
• Carbon-Carbon Bond Forming Reaction of Diketene with Benzaldehyde Catalyzed by Aluminum Alkoxides and Its Application to Asymmetric Reaction by Use of Diisopropyl L(+)-Tartrate-Aluminum Complexes
  作者：Hiroyuki Fujii、Naomi Watanabe、Masahiko Hayashi、Nobuki Oguni

  DOI：10.1080/00397919408010247

  日期：1994.12

  Abstract The reaction of diketene with benzaldehyde by use of aluminum alkoxides as a promoter yielded 5-hydroxy-3-oxoester and its application to enantioselective reaction was described.

  摘要 描述了以烷氧基铝为促进剂的双烯酮与苯甲醛反应生成5-羟基-3-氧代酯及其在对映选择性反应中的应用。
• 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。
• Phosphine-Catalyzed Synthesis of 1,3-Dioxan-4-ylidenes
  作者：Xue-Feng Zhu、Christopher E. Henry、Jay Wang、Travis Dudding、Ohyun Kwon

  DOI：10.1021/ol050203y

  日期：2005.3.1

  A phosphine-catalyzed reaction of an allenoate with aldehydes furnished (2,6-diaryl-[1,3]dioxan-4-ylidene)-acetates 4 in excellent to moderate yields with complete diastereoselectivity and high E/Z-selectivities. Upon removal of the acetal functionality in this domino reaction product 4, delta-hydroxy-beta-ketoester 11 was obtained. The reported vinylphosphonium-based approach provides a new way to achieve a synthesis of 6-hydroxy-beta-ketoesters that differs from the classical dianion-based approach.
• Salicylaldehyde Schiff bases derived from 2-ferrocenyl-2-amino alcohols. Part 2: Stereochemical divergence in the titanium-promoted enantioselective diketene addition to benzaldehyde
  作者：Rosa Ma Moreno、Albert Moyano

  DOI：10.1016/j.tetasy.2006.03.017

  日期：2006.4

  Chiral Schiff bases arising from the condensation of a set of diversely substituted (S)-2-amino-2-ferrocenyl ethanol derivatives 1a-e with salicylaldehydes 2A-B have been tested in the asymmetric, titanium-promoted diketene addition to benzaldehyde. This study has revealed that the enantiofacial selectivity of this reaction depends strongly on the substitution pattern of the amino alcohol component. Molecular mechanics calculations have led to the identification of a transition state model that explains these observations. (c) 2006 Elsevier Ltd. All rights reserved.