chlorodimethyl(4-pentenyl)silane | 33932-64-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: chlorodimethyl(4-pentenyl)silane
• 英文别名: Dimethyl-4-pentenyl-(1)-chlorsilan；Chloro(dimethyl)(pent-4-en-1-yl)silane；chloro-dimethyl-pent-4-enylsilane
• CAS: 33932-64-8
• 化学式: C₇H₁₅ClSi
• 分子量: 162.735
• InChiKey: KOHUASMRQIYLCF-UHFFFAOYSA-N

物化性质

• 沸点：
  160.2±19.0 °C(Predicted)
• 密度：
  0.873±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  chlorodimethyl(4-pentenyl)silane 在 lithium aluminium tetrahydride 作用下， 生成 (4-戊-1-烯基)二甲基硅烷
  参考文献：
  名称：

  Kobrakov,K.I. et al., Doklady Chemistry, 1971, vol. 198, p. 527 - 530

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-二甲基-1-硅杂-3-环己烯 在 盐酸 作用下， 以80%的产率得到chlorodimethyl(4-pentenyl)silane
  参考文献：
  名称：

  3-硅双环[3.1.0]己烷的热异构化：硅环戊烯和硅环己烯的新途径

  摘要：

  通过热解，3-硅双环[3.1.0]己烷导致硅环己烯成为主要产物，同时也导致硅环戊烯。不同异构硅环的比例在很大程度上取决于C（1）和C（5）取代基（R，R'= H，Me）的性质。

  DOI：

  10.1016/0022-328x(84)85138-4

文献信息

• <scp>Iron‐Catalyzed</scp> Reductive C(aryl)—Si <scp>Cross‐Coupling</scp> of Diaryl Ethers with Chlorosilanes
  作者：Pei Liu、Baowei Wu、Xuefeng Cong、Jie Kong

  DOI：10.1002/cjoc.202300593

  日期：2024.3.15

  shows high activity in the successive cleavage of unactivated C(aryl)—O bonds of diaryl ethers and strong electrophilic Si—Cl bonds of chlorosilanes, allowing their cross-coupling in a reductive fashion. The low-valent iron species generated in situ by reduction of FeCl2 with iPrMgCl was proposed, which prefers to initially cleavage the C(aryl)—O bond of diaryl ethers with the chelation help of an o-amide

  C(芳基)-O和Si-Cl键之间的还原交叉偶联作为构建C(芳基)-Si键的有价值的策略非常重要，但仍然是一个巨大的挑战。在此，我们报道了二芳基醚和氯硅烷通过铁催化的强亲电子C(芳基)-O和Si-Cl键断裂进行还原交叉偶联，这构成了合成一系列官能化芳基硅烷的有效方案。低成本FeCl 2 作为预催化剂和PrMgCl作为还原剂的组合在二芳基醚未活化的C(芳基)-O键和氯硅烷的强亲电Si-Cl键的连续断裂中表现出高活性，允许它们以还原的方式交叉耦合。提出了用 PrMgCl 还原 FeCl 2 原位生成低价铁物种，该物种倾向于在邻酰胺的螯合帮助下首先裂解二芳基醚的 C(芳基)-O 键辅助的。
• The far-UV photochemistry of five- and six-membered-ring monosilacycloalkenes in alcohols: stereospecific .beta.-cleavage to silyl ethers and stereoselective formation of silacycloalkyl ethers
  作者：Mark G. Steinmetz、Changjun Yu

  DOI：10.1021/jo00037a030

  日期：1992.5

  Photoalcoholysis of 1,1-dimethylsilacyclopent-2-ene (9) at 214 nm in methanol, 2,2,2-trifluoroethanol, and tert-butyl alcohol affords alkoxy(3-butenyl)dimethylsilanes 11 and 3-alkoxy-1,1-dimethylsilacyclopentanes 12. Also formed are alkoxy(cyclopropylmethyl)silanes 13 from apparent 1,3-C migration. In pure, deuterated alcohols (CH3OD and CF3CD2OD) adducts It and 12 become trans deuterated, whereas in dilute solutions of methanol-O-d in pentane, scrambling of deuterium between the trans and cis C-2 positions of 12 is observed without corresponding loss of stereospecificity for formation of silyl ether 11. Silyl ether 11 is thus produced via a pathway which is mechanistically distinct from that giving 12, for which the loss of stereoselectivity in dilute alcohols is ascribed to pseudorotational scrambling of deuterium in a silacyclopentyl cation intermediate. At high concentrations of alcohol the trans-stereoselective deuteration of 12 can be attributed to least hindered anti attack of the alcohol at C-3 of this hyperconjugatively stabilized cation. High cis-stereoselective deuteration of 12 is observed for photolysis in dilute CF3CD2OD in pentane, possibly reflecting the intermediacy of an ion pair or unsymmetrically solvated silacyclopentyl cation. Photoalcoholyses of the silacyclohex-2-ene were conducted for comparison.
• The Preparation and Properties of Cyclic Six-Membered Silicon Compounds
  作者：Robert Benkeser、Stanley Smith、James Noe

  DOI：10.1021/jo01266a602

  日期：1968.2
• MANUEL, G.;FAUCHER, A.;MAZEROLLES, P., J. ORGANOMET. CHEM., 1984, 264, N 1-2, 127-133
  作者：MANUEL, G.、FAUCHER, A.、MAZEROLLES, P.

  DOI：——

  日期：——
• Thermal isomerization of 3-silabicyclo[3.1.0]hexanes: A new route to silacyclopentenes and silacyclohexenes
  作者：Georges Manuel、Alfréda Faucher、Pierre Mazerolles

  DOI：10.1016/0022-328x(84)85138-4

  日期：1984.3

  By thermolysis, 3-silabicyclo[3.1.0]hexanes lead to silacyclohexenes as major products and also to silacyclopentenes. The ratio of the different isomeric silicon rings is strongly dependent on the nature of the C(1) and C(5) substituents (R, R′ = H, Me).

  通过热解，3-硅双环[3.1.0]己烷导致硅环己烯成为主要产物，同时也导致硅环戊烯。不同异构硅环的比例在很大程度上取决于C（1）和C（5）取代基（R，R'= H，Me）的性质。