2-(1-Hydroxy-ethyl)-pent-4-enoic acid tert-butyl ester | 135748-01-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-(1-Hydroxy-ethyl)-pent-4-enoic acid tert-butyl ester
• 英文别名: t-Butyl 2-allyl-3-hydroxybutanoate；tert-butyl 2-(1-hydroxyethyl)pent-4-enoate
• CAS: 135748-01-5
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: SSGRCGCQOFHMSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-Hydroxy-ethyl)-pent-4-enoic acid tert-butyl ester 在 吡啶 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 为溶剂， 生成 Acetic acid 2-(3,5-bis-trifluoromethyl-benzylcarbamoyl)-1-methyl-pent-4-enyl ester
  参考文献：
  名称：

  4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

  摘要：

  A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1'H-spiro[indene-1,4'-piperidin]-1'-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C-2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3'R)-3'-methyl-1'H-spiro[indene-1,4'-piperidin]-1'-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.011
• 作为产物：
  描述：

  tert-butyl 2-acetyl-4-pentenoate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以40%的产率得到2-(1-Hydroxy-ethyl)-pent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  微生物减少中的立体化学控制。9. 用面包酵母对 2-Alkyl-3-oxobutanoate 进行非对映选择性还原

  摘要：

  面包师的酵母将 2-烷基-3-氧代丁酸（CH3COCHRCO2R'；R=甲基、乙基、丙基、炔丙基和烯丙基）的酯还原为相应的（S）-羟基酯，具有独特的立体选择性，而在 2羟基酯的-位是S(反)或R(syn)，这取决于酯的碳烷氧基部分中烷氧基的结构。通常，关于 2 位的立体选择性并不令人满意。一般来说，叔丁酯的还原在产物中占主导地位，而 1,1-二甲基丙酯的还原则发挥顺式优势。从酯的合理构象的角度讨论了这两种酯在非对映选择性方面的显着差异。

  DOI：

  10.1246/bcsj.62.1179

文献信息

• Optically active compounding having plural chiral centers and production
  申请人：Chisso Corporation

  公开号：US05411877A1

  公开（公告）日：1995-05-02

  An ester is caused to act on a 2-substituted-3-hydroxycarboxylic acid ester as a racemate in the presence of hydrolase under substantially anhydrous conditions to effect a transesterification resulting in the resolution. The compound thus resolved is converted to an optically active 2,6-cis-2,5,6-substituted-1,3-dioxan-4-one and the resulting compound is recrystallized to give optically active 5,6-anti-2,5,6-substituted-1,3-dioxan-4-one and 5,6-syn-2,5,6-substituted-1,3-dioxan-4-one. Thus an optically active compound having plural chiral centers. Further, an optically active 2,5,6-substituted-1,3-dioxan-4-one obtained by transesterification and recrystallization is reacted with an alcohol to produce an optically active 2-substituted-3-hydroxycarboxylic acid ester.

  在基本无水的条件下，通过酯酶使酯作用于2-取代-3-羟基羧酸酯的外消旋体，以实现转酯反应并进行拆分。因此，被分离的化合物被转化为具有光学活性的2,6-顺式-2,5,6-取代-1,3-二氧杂环-4-酮，并且所得化合物被重结晶以得到具有光学活性的5,6-反-2,5,6-取代-1,3-二氧杂环-4-酮和5,6-顺-2,5,6-取代-1,3-二氧杂环-4-酮。因此，得到具有多个手性中心的光学活性化合物。此外，通过转酯反应和重结晶获得的光学活性2,5,6-取代-1,3-二氧杂环-4-酮与醇反应，产生光学活性的2-取代-3-羟基羧酸酯。
• Optically active compounds having plural chiral centers and production
  申请人：Chisso Corporation

  公开号：US05348870A1

  公开（公告）日：1994-09-20

  An ester is caused to act on a 2-substituted-3-hydroxycarboxylic acid ester as a racemate in the presence of hydrolase under substantially anhydrous conditions to effect a transesterification resulting in the resolution. The compound thus resolved is converted to an optically active 2,6-cis-2,5,6-substituted-1,3-dioxan-4-one and the resulting compound is recrystallized to give optically active 5,6-anti-2,5,6-substituted-1,3-dioxan-4-one and 5,6-syn-2,5,6-substituted-1,3-dioxan-4-one. Thus an optically active compound having plural chiral centers. Further, an optically active 2,5,6-substituted-1,3-dioxan-4-one obtained by transesterification and recrystallization is reacted with an alcohol to produce an optically active 2-substituted-3-hydroxycarboxylic acid ester.

  通过酯对2-取代-3-羟基羧酸酯进行消旋作用，存在水解酶的情况下，在基本无水的条件下发生转酯化反应，从而导致分辨过程。因此，分辨出的化合物被转化为具有光学活性的2,6-顺式-2,5,6-取代-1,3-二氧杂环戊酮，并且通过再结晶得到具有光学活性的5,6-反式-2,5,6-取代-1,3-二氧杂环戊酮和5,6-顺式-2,5,6-取代-1,3-二氧杂环戊酮。因此，得到了具有多个手性中心的光学活性化合物。此外，通过转酯化和再结晶得到的光学活性2,5,6-取代-1,3-二氧杂环戊酮与醇反应，可以产生光学活性的2-取代-3-羟基羧酸酯。
• Optically active compounds having plural chiral centers and the production thereof
  申请人：Chisso Corporation

  公开号：EP0428392A2

  公开（公告）日：1991-05-22

  Optically active compounds, having a plurality of chiral centres, have the general formulae: or in which R', R2 and R4 are the same or are different and each is an alkyl, alkenyl or alkynyl group having up to 40 carbon atoms, the carbon chain of which may contain one or more of halogen, cyano, oxygen, nitrogen, silicon, sulfur and substituted or unsubstituted benzene, cyclohexane, pyridine, pyrimidine, pyridazine, pyrazine, dioxane or bicyclooctane ring 5; R3 is an alkyl, alkenyl or alkynyl groups having 3 to 40 carbon atoms ; X is hydrogen or an alkanoyl group having 2 to 40 carbon atoms; and the carbon atom with the sign, *, is an asymmetic carbon.

  具有多个手性中心的光学活性化合物的通式为 或 其中 R'、R2 和 R4 相同或不同，且各自为具有多达 40 个碳原子的烷基、烯基或炔基，其碳链可包含一个或多个卤素、氰基、氧、氮、硅、硫和取代或未取代的苯、环己烷、吡啶、嘧啶、哒嗪、吡嗪、二氧杂环或双环辛烷环 5； R3 是具有 3 至 40 个碳原子的烷基、烯基或炔基； X 是氢或具有 2 至 40 个碳原子的烷酰基； 符号 * 的碳原子为异构碳。
• NAKAMURA, KAORU;MIYAI, TAKEHIKO;NAGAR, ASHISH;OKA, SHINZABURO;OHNO, ATSUY+, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1179-1187
  作者：NAKAMURA, KAORU、MIYAI, TAKEHIKO、NAGAR, ASHISH、OKA, SHINZABURO、OHNO, ATSUY+

  DOI：——

  日期：——
• Processes for the preparation of optically active compounds having plural chiral centers
  申请人：Chisso Corporation

  公开号：EP0428392B1

  公开（公告）日：1998-05-27