(S,E)-2-methyl-4-phenyl-3-butenoic acid | 143317-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,E)-2-methyl-4-phenyl-3-butenoic acid
• 英文别名: (E,2S)-2-methyl-4-phenylbut-3-enoic acid
• CAS: 143317-48-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: WMNSNYYTGUANTL-FLOXNTQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,E)-2-methyl-4-phenyl-3-butenoic acid 以 乙醚 为溶剂， 反应 0.08h， 生成 (3S,6R,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(E,2S)-4-phenylbut-3-en-2-yl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
  参考文献：
  名称：

  Total Synthesis of Cryptophycins via a Chemoenzymatic Approach

  摘要：

  A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.

  DOI：

  10.1021/jo960972i
• 作为产物：
  描述：

  (E)-methyl 4-phenylbut-3-enoate 在 sodium azide 、 phosphate buffer 、 lithium diisopropyl amide 作用下， 以 水 为溶剂， 反应 120.42h， 生成 (S,E)-2-methyl-4-phenyl-3-butenoic acid
  参考文献：
  名称：

  Total Synthesis of Cryptophycins via a Chemoenzymatic Approach

  摘要：

  A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.

  DOI：

  10.1021/jo960972i

文献信息

• Direct Enantioselective and Regioselective Alkylation of β,γ-Unsaturated Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Kai Yu、Bukeyan Miao、Wenqi Wang、Armen Zakarian

  DOI：10.1021/acs.orglett.9b00587

  日期：2019.3.15

  Efficient asymmetric alkylation of β,γ-unsaturated carboxylic acids without prior functionalization is enabled by chiral lithium amides. Enantioselectivity is imparted by a putative mixed lithium amide–enediolate aggregate that acts a traceless auxiliary formed in situ, allowing for a direct asymmetric alkylation and a simple recovery of the chiral reagent.

  β，γ-不饱和羧酸的有效不对称烷基化无需事先官能化就可以通过手性锂酰胺实现。对映选择性是由假定的酰胺基-烯二醇锂混合聚集体赋予的，该聚集体发挥就地形成的无痕助剂的作用，允许直接不对称烷基化和简单回收手性试剂。
• Phosphorus ylide chemistry investigated for dihydrotachysterol2 metabolite side-chain synthesis the Wittig approach
  作者：Jaap C. Hanekamp、Rob Boer Rookhuisen、Hendrik J.T. Bos、Lambert Brandsma

  DOI：10.1016/s0040-4020(01)90124-3

  日期：1992.1

  the γ-oxido ylide of R-(3-hydroxy-2,3-dimethylbutyl)triphenylphosphonium iodide 4, to be used in the 25-hydroxylated DHT2 side-chain synthesis, was studied. The synthesis of the chiral phosphonium salt 4 was done in an overall yield of 73%. Condensation of the ylide with benzaldehyde afforded the olefin 11 in a 70% yield; no isomer was detected. Furthermore, some other useful phosphonium salts were

  研究了用于25-羟基化DHT 2侧链合成的R-（3-羟基-2,3-二甲基丁基）三苯基碘化4 4的γ-氧化内酯的行为。手性phospho盐4的合成以73％的总产率进行。内鎓盐与苯甲醛的缩合得到烯烃11，产率为70％。未检测到异构体。此外，合成了一些其他有用的phospho盐。
• Total Synthesis of Cryptophycins via a Chemoenzymatic Approach
  作者：Grzegorz M. Salamonczyk、Kang Han、Zhi-wei Guo、Charles J. Sih

  DOI：10.1021/jo960972i

  日期：1996.1.1

  A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.