(Z)-2-carbamoylvinyl(tri-n-butyl)tin

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-carbamoylvinyl(tri-n-butyl)tin
• 化学式: C₁₅H₃₁NOSn
• 分子量: 360.127
• InChiKey: XRBPFXGAANWFBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-carbamoylvinyl(tri-n-butyl)tin 、 (1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-(triisopropylsilyloxy)-6-[(2E)-3-phenylacryloxy]oct-1-ene 在 双(乙腈)氯化钯(II) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (2Z,4E,7S,8R,9R,10S)-8,10-dimethyl-7-(triisopropylsilyloxy)-9-[(2E)-3-phenylacryloxy]-dodec-2,4-dienamide
  参考文献：
  名称：

  Stereoselective synthesis of basiliskamides A and B via Prins cyclisation

  摘要：

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.024
• 作为产物：
  描述：

  三甲基铝 、 methyl (E)-3-(tributylstannyl)acrylate 在 ammonium chloride 作用下， 以 正己烷 、 苯 为溶剂， 以64%的产率得到(Z)-2-carbamoylvinyl(tri-n-butyl)tin
  参考文献：
  名称：

  一种蒽霉素的全合成。钯催化偶联反应在丙烯酸侧链连接中的应用

  摘要：

  反应 de stannanesvinyliques avec des [烷基-10 三氟甲磺酰氧基-2 tetrahydro-5,10,11,11a] pyrrolo [2,1-c] benzodiazepinedione-5,11

  DOI：

  10.1021/ja00196a055

文献信息

• Determination of the absolute stereochemistry of the antifungal antibiotic YM-47522 by the total synthesis of its enantiomer
  作者：Mikhail S. Ermolenko

  DOI：10.1016/s0040-4039(96)01466-9

  日期：1996.9

  The enantiomer 1 of the new antifungal antibiotic YM-47522 has been synthesized and found to be the antipode of the natural product. Thus, the absolute stereochemistry of the naturally occurring antibiotic YM-47522 was determined to be (7S, 8S, 9R, 10S).

  已经合成了新型抗真菌抗生素YM-47522的对映异构体1，它是天然产物的对映体。因此，确定天然存在的抗生素YM-47522的绝对立体化学为（7S，8S，9R，10S）。
• Total Synthesis of (−)-Basiliskamide B
  作者：Luiz C. Dias、Caroline da Costa S. Gonçalves

  DOI：10.1002/adsc.200700589

  日期：2008.5.5

  The total synthesis of the polyketide antibiotic (−)-basiliskamide B is described. The convergent asymmetric synthesis relies on the use of a diastereoselective ethyl ketone aldol reaction followed by a syn selective reduction of a β-hydroxy ketone and a Stille cross-coupling between a Z-vinylstannane and an E-vinyl iodide to establish the (Z,E)-dienamide moiety.

  描述了聚酮化合物抗生素（-）-basiliskamide B的全合成。会聚的不对称合成依赖于使用非对映选择性的乙基酮醛醇缩合反应，然后顺式选择性还原β-羟基酮和Z-乙烯基锡烷与E-乙烯基碘化物之间的Stille交叉偶联，以建立（Z， E）-二酰胺部分。
• Process for producing 2-carbon-substituted carbapenem derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05258509A1

  公开（公告）日：1993-11-02

  A process for producing a 2-(unsubstituted or carbon-substituted)-1-carbapen-2-em-3-carboxylic acid derivative, which comprises reacting a 2-trifluoromethanesulfonyloxy-1-carbapen-2-em-3-carboxylic acid derivative or the 1-carbapen-2-em-3-carboxylic acid derivative derived from a 2-oxo-1-carbapenam-3-carboxylic acid derivative and trifluoromethanesulfonic anhydride, and a stannane derivative in an inert solvent in the presence of a palladium compound and a salt.

  一种制备2-(未取代或碳取代)-1-卡巴喷-2-烯-3-羧酸衍生物的方法，包括在惰性溶剂中，在钯化合物和盐的存在下，反应2-三氟甲磺酸酯化的1-卡巴喷-2-烯-3-羧酸衍生物或由2-氧代-1-卡巴喷酰胺-3-羧酸衍生物得到的1-卡巴喷-2-烯-3-羧酸衍生物和锡烷衍生物以及三氟甲磺酸酐进行反应。
• Total Synthesis of Basiliskamides A and B
  作者：Darren J. Lipomi、Neil F. Langille、James S. Panek

  DOI：10.1021/ol048574m

  日期：2004.9.1

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).
• Total synthesis of (-)-basiliskamide A and NMR studies on the conversion of basiliskamide A to basiliskamide B
  作者：Luiz C. Dias、Caroline C. S. Gonçalves

  DOI：10.1590/s0103-50532010001000030

  日期：——

  We describe herein our approach to the total synthesis of the antifungal polyketide (-)- basiliskamide A, as well as H-1 NMR studies on the migration of the cinnamoyl side chain of basiliskamide A to form basiliskamide B in CDCl3 solution.