<2S-(2α,3β,4β)>-1-<(1,1-dimethylethoxy)carbonyl>-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-(1-methylethenyl)-3-pyrrolidineacetic acid ethyl ester | 82614-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: <2S-(2α,3β,4β)>-1-<(1,1-dimethylethoxy)carbonyl>-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-(1-methylethenyl)-3-pyrrolidineacetic acid ethyl ester
• 英文别名: tert-butyl (2S,3S,4S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(2-ethoxy-2-oxoethyl)-4-prop-1-en-2-ylpyrrolidine-1-carboxylate
• CAS: 82614-09-3
• 化学式: C₂₃H₄₃NO₅Si
• 分子量: 441.684
• InChiKey: RCWIMXDQABGECA-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  <2S-(2α,3β,4β)>-1-<(1,1-dimethylethoxy)carbonyl>-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-(1-methylethenyl)-3-pyrrolidineacetic acid ethyl ester 在 四丁基氟化铵 作用下， 生成 (2S,3S,4S)-3-Ethoxycarbonylmethyl-2-hydroxymethyl-4-isopropenyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  （+）-和（-）-α-链烷酸的对映选择性合成

  摘要：

  已通过对映和非对映选择性串联迈克尔反应方法建立了分别从D-和L-丝氨酸分别生成（+）-和（-）-α-链烷酸的简捷对映选择性路线，可在单个反应中构建三个手性中心阶段。

  DOI：

  10.1016/s0040-4039(00)97768-2
• 作为产物：
  描述：

  [2S-(2α,3β,4α)]-4-acetyl-1-benzyl-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-pyrrolidineacetic acid ethyl ester 在 氢气 作用下， 生成 <2S-(2α,3β,4β)>-1-<(1,1-dimethylethoxy)carbonyl>-2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-(1-methylethenyl)-3-pyrrolidineacetic acid ethyl ester
  参考文献：
  名称：

  （+）-和（-）-α-链烷酸的对映选择性合成

  摘要：

  已通过对映和非对映选择性串联迈克尔反应方法建立了分别从D-和L-丝氨酸分别生成（+）-和（-）-α-链烷酸的简捷对映选择性路线，可在单个反应中构建三个手性中心阶段。

  DOI：

  10.1016/s0040-4039(00)97768-2

文献信息

• Total synthesis of (−)-kainic acid and (+)-allo-kainic acid through SmI₂-mediated intramolecular coupling between allyl chloride and an α,β-unsaturated ester
  作者：Junya Suzuki、Natsumi Miyano、Shunpei Yashiro、Taiki Umezawa、Fuyuhiko Matsuda

  DOI：10.1039/c7ob01427a

  日期：——

  cyclized through SmI2-mediated reductive coupling between allyl chloride and an α,β-unsaturated ester, although little has been reported about SmI2-promoted C–C bond formation of an allyl chloride with an α,β-unsaturated ester. Selection of either the 3,4-cis- or 3,4-trans-selective cyclization can be accomplished simply by changing the additives from NiI2 to HMPA during reductive cyclization conducted in

  通过SmI 2介导的烯丙基氯与α，β-不饱和酯之间的还原偶联，可将3,4-二取代的吡咯烷环有效地环化，尽管关于SmI 2促进烯丙基氯与C，C形成C-C键的报道很少。 α，β-不饱和酯。通过在H 2 O-THF中进行还原环化过程中，将添加剂从NiI 2改为HMPA，可以简单地选择3,4-顺式或3,4-反式选择性环化。（-）-海藻酸和（+）-别铝的全合成-海藻酸，是在神经科学和神经药理学中用作有用分子探针的吡咯烷生物碱，是通过使用SmI 2促进的立体互补闭环反应来构建2,3,4-三取代吡咯烷骨架的类胡萝卜素而成功实现的。
• A new approach to kainoids through tandem Michael reaction methodology: application to the enantioselective synthesis of (+)- and (-)-.alpha.-allokainic acid and to the formal synthesis of (-)-.alpha.-kainic acid
  作者：Achille Barco、Simonetta Benetti、Giampiero Spalluto、Alberto Casolari、Gian P. Pollini、Vinicio Zanirato

  DOI：10.1021/jo00049a040

  日期：1992.11

  A convergent, one-pot construction of functionalized pyrrolidine ring systems has been developed. The method is based on a tandem Michael reaction initiated by an intermolecular conjugate addition of a nitrogen nucleophile to an electrophilic olefin followed by trapping of the generated enolate by a built-in alpha,beta-unsaturated acceptor. After model studies verified the feasibility of the process and gave information about its stereochemical outcome, the strategy was successfully applied to kainoid synthesis. The construction of the basic pyrrolidine skeleton of all the members of the family requires coupling of a suitable electrophilic subunit with a common donor-acceptor fragment containing the nitrogen nucleophile. Thus, the enantioselective synthesis of (+)-alpha-allokainic acid (2) and the formal synthesis of its C-4 epimer (-)-alpha-kainic acid (1), have been accomplished using methyl vinyl ketone and 2-nitro-3-methyl-1,3-butadiene, respectively, as electrophilic partners of (S)-4-(benzylamino)-5-hydroxy-2-pentenoic acid ethyl ester (17), easily derived in six steps from D-serine. Although the acetyl group of methyl vinyl ketone is a logical precursor to the isopropenyl moiety of 2, the use of the nitrobutadiene is more appropriate for the synthesis of 1 because of the startling degree of control of the cyclization stereochemistry exerted by the nitro group.
• Enantioselective synthesis and absolute configuration of (-)-.alpha.-kainic acid
  作者：Wolfgang Oppolzer、Klaus Thirring

  DOI：10.1021/ja00382a054

  日期：1982.9