(RR,SS)-2-hydroxy-2,3-dimethyl-4-pentenoic acid | 82731-64-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (RR,SS)-2-hydroxy-2,3-dimethyl-4-pentenoic acid
• 英文别名: 2-hydroxy-2,3-dimethylpent-4-enoic acid；(2S,3S)-2-hydroxy-2,3-dimethylpent-4-enoic acid
• CAS: 82731-64-4
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: PYXQIRRBOUWCLO-FSPLSTOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 (RR,SS)-2-hydroxy-2,3-dimethyl-4-pentenoic acid 在 盐酸 作用下， 生成 (2SR,3SR)-ethyl 2-hydroxy-2,3-dimethylpent-4-enoate
  参考文献：
  名称：

  Ester-enolate Claisen rearrangement of lactic acid derivatives

  摘要：

  DOI：

  10.1021/jo00141a025
• 作为产物：
  描述：

  (Z)-but-2-enyldiisopropoxyborane 、 丙酮酸 在 三乙胺 作用下， 生成 (RR,SS)-2-hydroxy-2,3-dimethyl-4-pentenoic acid
  参考文献：
  名称：

  α-氧代羧酸的立体选择性巴豆基硼化

  摘要：

  巴豆基硼酸酯与α-氧代羧酸以高度立体可控的方式反应。该反应大概通过双环过渡态进行。α-羧基取代基对反应的速率，区域选择性和立体选择性具有显着影响。形成均一的α-羟基羧酸，其区域和立体选择性接近100％。

  DOI：

  10.1016/s0040-4039(00)93527-5

文献信息

• Synthesis of γ,δ-Unsaturated Glycolic Acids via Sequenced Brook and Ireland−Claisen Rearrangements
  作者：Daniel C. Schmitt、Jeffrey S. Johnson

  DOI：10.1021/ol9029353

  日期：2010.3.5

  Organozinc, -magnesium, and -lithium nucleophiles initiate a Brook/Ireland−Claisen rearrangement sequence of allylic silyl glyoxylates resulting in the formation of γ,δ-unsaturated α-silyloxy acids.

  有机锌、-镁和-锂亲核试剂引发烯丙基乙醛酸甲硅烷基酯的布鲁克/爱尔兰-克莱森重排序列，导致形成 γ,δ-不饱和 α-甲硅烷氧基酸。
• A Highly Atom Efficient, Solvent Promoted Addition of Tetraallylic, Tetraallenic, and Tetrapropargylic Stannanes to Carbonyl Compounds
  作者：Adam McCluskey、I. Wayan Muderawan、Muntari、David J. Young

  DOI：10.1021/jo015904x

  日期：2001.11.1

  Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation. reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.
• Diastereo- and enantio-selective crotylation of α-ketoesters using crotyl boronic acid ester complexes
  作者：Yanping Chen、Laxman Eltepu、Paul Wentworth

  DOI：10.1016/j.tetlet.2004.09.082

  日期：2004.11

  A diastereo- and enantio-selective crotylation of ethyl pyruvate has been achieved using a chiral boronic acid auxiliary-based approach. This reaction creates two contiguous stereogenic centers, one of which is a quaternary carbon with complete diastereoselectivity and with enantioselectivities up to 7:1 (73% ee). (C) 2004 Published by Elsevier Ltd.
• Ester-enolate Claisen rearrangement of lactic acid derivatives
  作者：Paul A. Bartlett、Donna J. Tanzella、James F. Barstow

  DOI：10.1021/jo00141a025

  日期：1982.9
• The stereoselective crotylboration of alpha-oxocarboxylic acids
  作者：Zhe Wang、Xian-Jun Meng、George W. Kabalka

  DOI：10.1016/s0040-4039(00)93527-5

  日期：1991.10

  acids in a highly stereocontrolled manner. The reaction presumably proceeds through a bicyclic transition state. The alpha-carboxylic substituent exerts a remarkable effect on the rate, regio- and stereoselectivities of the reaction; homoallylic alpha-hydroxycarboxylic acids are formed with regio- and stereoselectivities approach 100%.

  巴豆基硼酸酯与α-氧代羧酸以高度立体可控的方式反应。该反应大概通过双环过渡态进行。α-羧基取代基对反应的速率，区域选择性和立体选择性具有显着影响。形成均一的α-羟基羧酸，其区域和立体选择性接近100％。