(2SR,3RS)-ethyl 2-hydroxy-2,3-dimethylpent-4-enoate | 82731-72-4

• 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: (2SR,3RS)-ethyl 2-hydroxy-2,3-dimethylpent-4-enoate
• 英文别名: ethyl (RS,SR)-2-hydroxy-2,3-dimethyl-4-pentenoate；ethyl (2R,3S)-2-hydroxy-2,3-dimethylpent-4-enoate
• CAS: 82731-72-4
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: GXDDCADFGIBZPQ-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (RS,SR)-2-hydroxy-2,3-dimethyl-4-pentynoate 生成 (2SR,3RS)-ethyl 2-hydroxy-2,3-dimethylpent-4-enoate
  参考文献：
  名称：

  BARTLETT, P. A.;TANZELLA, D. J.;BARSTOW, J. F., J. ORG. CHEM., 1982, 47, N 20, 3941-3945

  摘要：

  DOI：

文献信息

• Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation
  作者：Robert A. Batey、Avinash N. Thadani、David V. Smil

  DOI：10.1016/s0040-4039(99)00774-1

  日期：1999.6

  Potassium allyl- and crotyltrifluoroborates react rapidly with aldehydes in the presence of BF3·Et2O. These salts are stable to air and moisture, and lead to adducts in high yield and with high diastereoselectivity. The stereochemistry of the crotylated products is consistent with the reaction via allylboron difluoride and a Zimmerman-Traxler like transition state.

  在BF 3 ·Et 2 O的存在下，烯丙基三氟硼酸钾和巴豆基三氟硼酸钾与醛迅速反应。这些盐对空气和水分稳定，并以高收率和高非对映选择性生成加合物。丁酰化产物的立体化学与经由二氟化烯丙基硼和Zimmerman-Traxler样过渡态的反应一致。
• Allylation and Crotylation of Ketones and Aldehydes Using Potassium Organotrifluoroborate Salts under Lewis Acid and Montmorillonite K10 Catalyzed Conditions
  作者：Farhad Nowrouzi、Avinash N. Thadani、Robert A. Batey

  DOI：10.1021/ol900599q

  日期：2009.6.18

  Two convenient highly diastereoselective protocols for the allylation and crotylation of ketones using practical, air- and water-stable potassium allyl and crotyltrifluoroborate salts have been developed. BF3·OEt2 and montmorillonite clay are used as catalysts to promote additions. The montmorillonite-catalyzed method in particular is very robust, providing a straightforward and scalable method for

  已经开发了两种方便的高度非对映选择性方案，用于使用实用的，对空气和水稳定的烯丙基钾盐和巴豆基三氟硼酸盐进行烯丙基化和丁酰化。BF 3 ·OEt 2和蒙脱土用作促进添加的催化剂。蒙脱石催化的方法尤其非常健壮，它为多种酮和醛的烯丙基化和丁烯酰化提供了一种简单易行的方法。
• Allyl Transfer to Aldehydes and Ketones by Brønsted Acid Activation of Allyl and Crotyl 1,3,2-Dioxazaborolidines
  作者：Maureen K. Reilly、Scott D. Rychnovsky

  DOI：10.1021/ol1020515

  日期：2010.11.5

  Brønsted acids activate allyl dioxazaborolidines to generate reactive allyl-transfer reagents in situ. These reagents add to aldehydes and ketones to generate the corresponding alcohols in good yields under mild conditions. The E- and Z-crotyl reagents react diastereoselectively with aldehydes and ketones to produce anti and syn adducts, respectively, a result consistent with a cyclic transition state (type

  烷基二恶唑硼烷是空气稳定的，通常是结晶有机硼烷。多种 Brønsted 酸激活烯丙基二恶唑硼烷以原位生成反应性烯丙基转移试剂。这些试剂添加到醛和酮中，在温和的条件下以良好的收率生成相应的醇。的ë -和Ž -crotyl试剂与醛和酮非对映选择性反应以产生抗与顺式加合物，分别与环状过渡态（I型机构）相一致的结果。
• 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.
• 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