(S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one | 156093-90-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one
• 英文别名: (S)-3-(tert-butyldimethylsilyloxy)-1-chloro-2-butanone；(S)-1-chloro-3-(tert-butyldimethylsilyloxy)butan-2-one；(3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-chlorobutan-2-one
• CAS: 156093-90-2
• 化学式: C₁₀H₂₁ClO₂Si
• 分子量: 236.814
• InChiKey: VRHCDDYURGXJCS-QMMMGPOBSA-N

物化性质

• 沸点：
  237.3±20.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one 在 potassium tert-butylate 作用下， 生成 2-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-butylidene]-malonic acid diethyl ester
  参考文献：
  名称：

  从（3-烷氧基羰基-2-氧代亚丙基）三苯基膦烷和1,2-二酰基乙烯单步合成环戊烯酮

  摘要：

  （3-烷氧基羰基-2-氧代亚丙基）三苯基膦烷与1，2-二丙烯基乙烯反应生成环戊烯酮。手性酰基亚甲基丙二酸酯的使用导致以高度非对映选择性的方式形成旋光的环戊烯酮。

  DOI：

  10.1016/0040-4039(95)02186-8
• 作为产物：
  描述：

  (s)-(-)-2-(叔丁基二甲基甲硅烷基氧基)丙酸乙酯 以89%的产率得到
  参考文献：
  名称：

  Baruenga Jose, Baragana Beatriz, Alonso Alejandro, Concellon Jose M., J. Chem. Soc. Chem. Commun, (1994) N 8, S 969-970

  摘要：

  DOI：

文献信息

• The first direct preparation of chiral functionalised ketones and their synthetic uses
  作者：José Barluenga、Beatriz BaragañA、Alejandro Alonso、José M. Concellón

  DOI：10.1039/c39940000969

  日期：——

  Almost enantiomerically pure halogenated α-hydroxy and α-amino ketones can be prepared from O-protected lactates and tribenzylated alanine, respectively; whilst amino ketones 3g have also been transformed into the amino epoxide 7 with high diastereoselectivity.

  几乎纯镜像异构体的卤代α-羟基和α-氨基酮分别可以通过O-保护的乳酸盐和三苄基化的丙氨酸制备；同时，氨基酮3g也已高度立体选择性地转化为氨基环氧化物7。
• Diastereoselective reduction of (S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2S,3R) and (2S,3S) O-tert-butyldimethylsilyl-3,4-epoxybutan-2-ol
  作者：JoséM. Concellón、Pablo L. Bernad、R. Alvarez、A. Rodríguez、B. Baragaña

  DOI：10.1016/s0040-4039(99)00313-5

  日期：1999.4

  (2S,3S)- And (2R,3S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-ol have been obtained with high diastereoselectivity by reduction of enantiopure (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corresponding (2R,3S)- and (2S,3S)-3-[(tert-butyldimethyl)silyloxy]-1,2-epoxybutane. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (2S,3S)- 和 (2R,3S)-3-[(叔丁基二甲基)硅氧基]-1-氯丁烷-2-醇已通过对映纯 (S)-3-[(叔丁基二甲基)硅氧基]-1-氯丁烷-2-酮使用不同的还原剂进行还原，获得高非对映选择性。这些手性醇被转化为相应的 (2R,3S)- 和 (2S,3S)-3-[(叔丁基二甲基)硅氧基]-1,2-环氧丁烷。© 1999 Elsevier Science Ltd. 保留所有权利。
• Optically active halohydrin derivative and process for producing optically active epoxy alcohol derivative from the same
  申请人：Okuro Kazumi

  公开号：US20060155136A1

  公开（公告）日：2006-07-13

  The present invention provides an industrially safe, easily operable process for producing an optically active epoxy alcohol derivative useful as an intermediate for pharmaceuticals from inexpensively available materials, and also provides a novel halohydrin derivative serving as an important intermediate for the epoxy alcohol derivative. Furthermore, the present invention provides a process for producing an intermediate for a triazole antifungal agent by allowing a halohydrin to react with a triazole sulfonamide, the process including a small number of steps. A process for producing an optically active epoxy alcohol derivative includes allowing an optically active α-substituted propionate derivative to react with a haloacetic acid derivative in the presence of a base to prepare an optically active haloketone derivative, allowing the resulting haloketone derivative to react with an aryl metal compound to stereoselectively prepare a halohydrin derivative, eliminating a substituent for the hydroxy group of the halohydrin derivative, and performing epoxidation with a base. Furthermore, a process for producing an intermediate for a triazole antifungal agent includes allowing a halohydrin derivative to react with a triazole sulfonamide, the process including a small number of steps.

  本发明提供了一种工业安全、易于操作的过程，用于从价格便宜的原料中生产有用于制药中间体的光学活性环氧醇衍生物，并提供了一种新型的卤代醇衍生物，作为环氧醇衍生物的重要中间体。此外，本发明提供了一种通过让卤代醇与三唑磺酰胺反应来生产三唑类抗真菌剂中间体的过程，包括少量的步骤。生产光学活性环氧醇衍生物的过程包括在碱的存在下让光学活性α-取代丙酸酯衍生物与卤代乙酸衍生物反应，以制备光学活性卤代酮衍生物，让产生的卤代酮衍生物与芳基金属化合物反应，选择性地立体定向制备卤代醇衍生物，消除卤代醇衍生物的羟基取代基，并在碱的存在下进行环氧化。此外，生产三唑类抗真菌剂中间体的过程包括让卤代醇衍生物与三唑磺酰胺反应，该过程包括少量的步骤。
• Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides
  作者：Mariam Traoré、Flore Mietton、Danièle Maubon、Marine Peuchmaur、Flaviane Francisco Hilário、Rossimiriam Pereira de Freitas、Alexandre Bougdour、Aurélie Curt、Marjorie Maynadier、Henri Vial、Hervé Pelloux、Mohamed-Ali Hakimi、Yung-Sing Wong

  DOI：10.1021/jo4001492

  日期：2013.4.19

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.
• OPTICALLY ACTIVE HALOHYDRIN DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE EPOXY ALCOHOL DERIVATIVE FROM THE SAME
  申请人：KANEKA CORPORATION

  公开号：EP1647551B1

  公开（公告）日：2011-05-04