(3-dimethylaminopropyl)triphenylstannane | 60385-55-9

• 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: (3-dimethylaminopropyl)triphenylstannane
• 英文别名: N,N-dimethyl-3-triphenylstannylpropan-1-amine
• CAS: 60385-55-9
• 化学式: C₂₃H₂₇NSn
• 分子量: 436.184
• InChiKey: CXYDUWFIZOYBKN-UHFFFAOYSA-N

物化性质

• 沸点：
  464.2±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3-dimethylaminopropyl)triphenylstannane 在 C₆H₅OH 作用下， 以 甲苯 为溶剂， 以86%的产率得到(3-dimethylaminopropyl)phenoxydiphenylstannane
  参考文献：
  名称：

  Utilization of hypervalently activated organotin compounds in synthesis. Preparation and reactions of Me2N(CH2)3SnPh3

  摘要：

  The reaction of Me2N(CH2)3SnPh3 (1) with phenol gives Me2N(CH2)3Sn(OPh)nPh(3-n) (2, n = 1; 3, n = 2) in good yields. All the phenyl groups are cleaved off when 1 is treated with glycol or pinacol, resulting in the formation of [Me2N(CH2)3Sn]2(OC2H4O)3 (4) and [Me2N(CH2)3Sn]2(OC2Me4O)3 (5), respectively. Compounds 4 and 5 are transformed almost quantitatively into Me2N(CH2)3Sn(SPh)3 (6) and [Me2N(CH2)3SnCl4]-H+ (7) by reaction with phenyl mercaptan and trimethylchlorosilane, respectively. The reaction of 2 with triethanolamine and nitrilotriacetic acid affords the new stannatrane Me2N(CH2)3Sn(OCH2CH2)3N (8) and Me2N(CH2)3Sn(OCOCH2)3N (9), respectively. However, the N-oxide derivative Me2(O)N(CH2)3Sn(OCOCH2)3N (10) is obtained by reaction of 1 with N(CH2COOH)3 in DMF. Compounds 1-10 have been characterized by means of H-1, C-13 and Sn-119 NMR spectroscopy and mass spectrometry. The crystal structures of Me2N(CH2)3Sn(SPh)3 (6) and Me2(O)N(CH2)3Sn(OCOCH2)3N (10) have been determined by an X-ray diffraction study. The tin atom in 6 is trigonal bipyramidal with an intramolecular Sn-N distance of 2.605(6) angstrom. Compound 10 contains an octahedral tin with intramolecular Sn-N and Sn-ON distances of 2.231(7) and 2.101(7) angstrom, respectively.

  DOI：

  10.1016/0022-328x(93)80454-j
• 作为产物：
  描述：

  magnesium,N,N-dimethylpropan-1-amine,chloride 、 三苯基氯化锡 以 四氢呋喃 为溶剂， 以70%的产率得到(3-dimethylaminopropyl)triphenylstannane
  参考文献：
  名称：

  Utilization of hypervalently activated organotin compounds in synthesis. Preparation and reactions of Me2N(CH2)3SnPh3

  摘要：

  The reaction of Me2N(CH2)3SnPh3 (1) with phenol gives Me2N(CH2)3Sn(OPh)nPh(3-n) (2, n = 1; 3, n = 2) in good yields. All the phenyl groups are cleaved off when 1 is treated with glycol or pinacol, resulting in the formation of [Me2N(CH2)3Sn]2(OC2H4O)3 (4) and [Me2N(CH2)3Sn]2(OC2Me4O)3 (5), respectively. Compounds 4 and 5 are transformed almost quantitatively into Me2N(CH2)3Sn(SPh)3 (6) and [Me2N(CH2)3SnCl4]-H+ (7) by reaction with phenyl mercaptan and trimethylchlorosilane, respectively. The reaction of 2 with triethanolamine and nitrilotriacetic acid affords the new stannatrane Me2N(CH2)3Sn(OCH2CH2)3N (8) and Me2N(CH2)3Sn(OCOCH2)3N (9), respectively. However, the N-oxide derivative Me2(O)N(CH2)3Sn(OCOCH2)3N (10) is obtained by reaction of 1 with N(CH2COOH)3 in DMF. Compounds 1-10 have been characterized by means of H-1, C-13 and Sn-119 NMR spectroscopy and mass spectrometry. The crystal structures of Me2N(CH2)3Sn(SPh)3 (6) and Me2(O)N(CH2)3Sn(OCOCH2)3N (10) have been determined by an X-ray diffraction study. The tin atom in 6 is trigonal bipyramidal with an intramolecular Sn-N distance of 2.605(6) angstrom. Compound 10 contains an octahedral tin with intramolecular Sn-N and Sn-ON distances of 2.231(7) and 2.101(7) angstrom, respectively.

  DOI：

  10.1016/0022-328x(93)80454-j

文献信息

• Nucleophilic attack within Ge, Sn and Pb complexes containing Me2N(CH2)3—as a potential intramolecular donor ligand
  作者：Andrea Zickgraf、Mike Beuter、Ute Kolb、Martin Dräger、Ramon Tozer、Dainis Dakternieks、Klaus Jurkschat

  DOI：10.1016/s0020-1693(98)00071-1

  日期：1998.7
• Directed cleavage of carbon—tin bonds by palladium
  作者：J.William Suggs、Ken.S. Lee

  DOI：10.1016/0022-328x(86)84004-9

  日期：1986.1
• MEGANEM, F., J. IRAGI CHEM. SOC., 1980, 5, N ISSUE, 202-209
  作者：MEGANEM, F.

  DOI：——

  日期：——
• Utilization of hypervalently activated organotin compounds in synthesis. Preparation and reactions of Me2N(CH2)3SnPh3
  作者：Dainis Dakternieks、Gail Dyson、Klaus Jurkschat、Ramon Tozer、Edward R.T. Tiekink

  DOI：10.1016/0022-328x(93)80454-j

  日期：1993.10

  The reaction of Me2N(CH2)3SnPh3 (1) with phenol gives Me2N(CH2)3Sn(OPh)nPh(3-n) (2, n = 1; 3, n = 2) in good yields. All the phenyl groups are cleaved off when 1 is treated with glycol or pinacol, resulting in the formation of [Me2N(CH2)3Sn]2(OC2H4O)3 (4) and [Me2N(CH2)3Sn]2(OC2Me4O)3 (5), respectively. Compounds 4 and 5 are transformed almost quantitatively into Me2N(CH2)3Sn(SPh)3 (6) and [Me2N(CH2)3SnCl4]-H+ (7) by reaction with phenyl mercaptan and trimethylchlorosilane, respectively. The reaction of 2 with triethanolamine and nitrilotriacetic acid affords the new stannatrane Me2N(CH2)3Sn(OCH2CH2)3N (8) and Me2N(CH2)3Sn(OCOCH2)3N (9), respectively. However, the N-oxide derivative Me2(O)N(CH2)3Sn(OCOCH2)3N (10) is obtained by reaction of 1 with N(CH2COOH)3 in DMF. Compounds 1-10 have been characterized by means of H-1, C-13 and Sn-119 NMR spectroscopy and mass spectrometry. The crystal structures of Me2N(CH2)3Sn(SPh)3 (6) and Me2(O)N(CH2)3Sn(OCOCH2)3N (10) have been determined by an X-ray diffraction study. The tin atom in 6 is trigonal bipyramidal with an intramolecular Sn-N distance of 2.605(6) angstrom. Compound 10 contains an octahedral tin with intramolecular Sn-N and Sn-ON distances of 2.231(7) and 2.101(7) angstrom, respectively.