methyl 3,3-bis(tributylstannyl)propionate | 21785-86-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: methyl 3,3-bis(tributylstannyl)propionate
• CAS: 21785-86-4
• 化学式: C₂₈H₆₀O₂Sn₂
• 分子量: 666.203
• InChiKey: JIIVKFLUMCVDGH-UHFFFAOYSA-N

物化性质

• 沸点：
  557.9±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.16
• 重原子数：
  32
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 methyl 3,3-bis(tributylstannyl)propionate 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  Conformational Investigations of Ester-Functionalized gem-Distannyl Derivatives by ¹H−¹¹⁹Sn Correlation NMR

  摘要：

  The conformational dependence on temperature and concentration of methyl 3,3-bis(tributylstannyl)propionate compounds of the type (Bu3Sn)(2)CH-CHR-CO2Me (R = H, 1; R = CH2CH=CH2, 2; R = CH2Ph, 3; R = CH2NMe2, 5) was studied by means of Karplus-type dihedral angle relations for (3)J(Sn-119-C-13) couplings from C-13 NMR spectra and (3)J(Sn-119-H-1) couplings from H-1-Sn-119 correlation NMR experiments, assisted by O-17 and Sn-119 NMR spectroscopy. The results from these structural investigations point toward a dominant conformation in which a very weak tin-carbonyl oxygen Sn<--O=C-O interaction is possible.

  DOI：

  10.1021/om980964n
• 作为产物：
  描述：

  叔丁基锡烷 、 丙炔酸甲酯 在 苄基三乙基氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以91%的产率得到methyl 3,3-bis(tributylstannyl)propionate
  参考文献：
  名称：

  Novel Method of Three-Carbon Elongation Using Bis(tributylstannyl)propanol

  摘要：

  The reaction of Me3SiSnBu3 (1) with methyl propiolate in DMF in the presence of BnEt3NCl gave methyl 3, 3-bis(tributylstannyl)propionate (7) in high yield. Reduction of 7 with LiAlH4 followed by treatment with MOMCl gave 3,3-bis(tributylstannyl)propanol derivative 17d in a quantitative yield, which was a useful reagent for C-3 unit elongation. Treatment of 17d with BuLi in THF in the presence of HMPA gave alpha-stannylated carbanion II, which reacted with various electrophiles, such as aldehydes, ketones, esters, and alkyl halides, to give C-3 elongation products III.

  DOI：

  10.1021/jo970844+

文献信息

• Highly Stereocontrolled Cyclopropanation by the 1,3-Elimination of a Bis(tributylstannyl)propanol Derivative
  作者：Naohiro Isono、Miwako Mori

  DOI：10.1021/jo960981r

  日期：1996.1.1

  The highly stereoselective ring closure of gamma-hydroxystannyl derivative was realized. The aldol reaction of methyl bis(tributylstannyl)propionate (2) with aldehyde 5 proceeds stereoselectively to give (gamma-hydroxypropyl)stannane 6, and the cyclopropanation reaction of aldol product 6 proceeds smoothly in a highly stereoselective manner presumably via a W-shape transition state. The stannyl group

  实现了γ-羟基锡烷基衍生物的高度立体选择性的闭环。双（三丁基锡烷基）丙酸甲酯（2）与醛5的醛醇缩合反应立体选择性生成（γ-羟丙基）锡烷6，醛醇产物6的环丙烷化反应以高度立体选择性的方式顺利进行，大概是通过W形跃迁进行的州。环丙烷环上的苯乙烯基可以保留构型而转化为各种亲电试剂。结果，可以高收率获得各种立体控制的1,2,3-三取代的环丙烷。
• On the chemospecificity of the double stannylation and double hydrostannation of terminal alkynes by the tributylstannane in the presence of thiol
  作者：Jean-Charles Meurice、Martine Vallier、Max Ratier、Jean-Georges Duboudin、Michel Pétraud

  DOI：10.1016/s0022-328x(97)00283-0

  日期：1997.9

  The mechanism of competing double stannylation and double hydrostannation reactions of terminal alkynes in the presence of arylthiol has been investigated. The data reveal the radical character of the reactions, the importance of the [tributylstannane/arylthiol] system as radical initiator at ambient temperature and the occurrence of a polarity reversal catalysis process in the double hydrostannation pathway. (C) 1997 Elsevier Science S.A.
• SEITZ, D. E.;LEE, SHI-HUNG, TETRAHEDRON LETT., 1981, 22, N 49, 4909-4912
  作者：SEITZ, D. E.、LEE, SHI-HUNG

  DOI：——

  日期：——
• Novel Method of Three-Carbon Elongation Using Bis(tributylstannyl)propanol
  作者：Naohiro Isono、Miwako Mori

  DOI：10.1021/jo970844+

  日期：1998.3.1

  The reaction of Me3SiSnBu3 (1) with methyl propiolate in DMF in the presence of BnEt3NCl gave methyl 3, 3-bis(tributylstannyl)propionate (7) in high yield. Reduction of 7 with LiAlH4 followed by treatment with MOMCl gave 3,3-bis(tributylstannyl)propanol derivative 17d in a quantitative yield, which was a useful reagent for C-3 unit elongation. Treatment of 17d with BuLi in THF in the presence of HMPA gave alpha-stannylated carbanion II, which reacted with various electrophiles, such as aldehydes, ketones, esters, and alkyl halides, to give C-3 elongation products III.
• Conformational Investigations of Ester-Functionalized <i>gem</i>-Distannyl Derivatives by ¹H−¹¹⁹Sn Correlation NMR
  作者：Jean-Charles Meurice、Jean-Georges Duboudin、Max Ratier、Michel Pétraud、Rudolph Willem、Monique Biesemans

  DOI：10.1021/om980964n

  日期：1999.4.1

  The conformational dependence on temperature and concentration of methyl 3,3-bis(tributylstannyl)propionate compounds of the type (Bu3Sn)(2)CH-CHR-CO2Me (R = H, 1; R = CH2CH=CH2, 2; R = CH2Ph, 3; R = CH2NMe2, 5) was studied by means of Karplus-type dihedral angle relations for (3)J(Sn-119-C-13) couplings from C-13 NMR spectra and (3)J(Sn-119-H-1) couplings from H-1-Sn-119 correlation NMR experiments, assisted by O-17 and Sn-119 NMR spectroscopy. The results from these structural investigations point toward a dominant conformation in which a very weak tin-carbonyl oxygen Sn<--O=C-O interaction is possible.