6-methoxy-2,2-dimethyl-4-methylene-4H-<1,3,2>dioxasiline | 130573-42-1

• 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: 6-methoxy-2,2-dimethyl-4-methylene-4H-<1,3,2>dioxasiline
• 英文别名: 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene；4-methoxy-2,2-dimethyl-6-methylidene-1,3,2-dioxasiline
• CAS: 130573-42-1
• 化学式: C₇H₁₂O₃Si
• 分子量: 172.256
• InChiKey: RSMOIKBLVOSJQK-UHFFFAOYSA-N

物化性质

• 沸点：
  169.6±29.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-methoxy-2,2-dimethyl-4-methylene-4H-<1,3,2>dioxasiline 生成 6-methoxy-2,2-dimethyl-3H-oxasilin-4-one
  参考文献：
  名称：

  The formal oxidative addition of electron-rich transoid dienes to bromonaphthoquinones

  摘要：

  This work established the idea that a halogen atom, such as bromine, will act as a control element in the regiospecific formation of a new carbon-carbon bond. The addition of the electron-rich end of a transoid diene to a bromojuglone derivative occurred exclusively at the unsubstituted carbon of the quinone. Thus, 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene (3) and either 2- or 3-bromo-5-hydroxy-1,4-naphthoquinone (1 or 2) afforded the adducts 19 or 20 in 57% or 71% yield. Similarly, 2,2-dimethyl-6-methylene-4-(trimethylsiloxy)-1,3-diox-4-ene (4) and 1 gave 21 in 77% yield.

  DOI：

  10.1021/jo00001a020
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 二氯二甲基硅烷 生成 6-methoxy-2,2-dimethyl-4-methylene-4H-<1,3,2>dioxasiline
  参考文献：
  名称：

  The formal oxidative addition of electron-rich transoid dienes to bromonaphthoquinones

  摘要：

  This work established the idea that a halogen atom, such as bromine, will act as a control element in the regiospecific formation of a new carbon-carbon bond. The addition of the electron-rich end of a transoid diene to a bromojuglone derivative occurred exclusively at the unsubstituted carbon of the quinone. Thus, 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene (3) and either 2- or 3-bromo-5-hydroxy-1,4-naphthoquinone (1 or 2) afforded the adducts 19 or 20 in 57% or 71% yield. Similarly, 2,2-dimethyl-6-methylene-4-(trimethylsiloxy)-1,3-diox-4-ene (4) and 1 gave 21 in 77% yield.

  DOI：

  10.1021/jo00001a020

文献信息

• Attachment of Ketide Side Chains on Methyl-1,4-naphthoquinones for biomimetic type angucycline syntheses
  作者：K. Krohn、N. Böker

  DOI：10.1002/prac.19973390123

  日期：——

  The Michael addition of nucleophiles 5-10 derived from beta-ketoesters with the methyl-1,4-naphthoquinones 16 and 20 was systematically investigated in connection with a biomimetic type synthesis of angucyclinone antibiotics. Drawbacks of these reactions were the formation of regioisomers (e.g. 12/13 and 18/19), unwanted cyclizations (14 and 15), and occasional 1,2-addition (23). No side reactions and a good overall yield (80%) in the attachment of a C-3-2-oxoside chain was achieved by Stille reaction of allyl stannane 11 with the bromoquinone 24 followed by cleavage of the double bond to yield ketone 26.
• GRUNWELL, JOHN R.;KARIPIDES, ANASTAS;WIGAL, CARL T.;HEINZMAN, STEPHEN W.;+, J. ORG. CHEM., 56,(1991) N, C. 91-95
  作者：GRUNWELL, JOHN R.、KARIPIDES, ANASTAS、WIGAL, CARL T.、HEINZMAN, STEPHEN W.、+

  DOI：——

  日期：——
• The formal oxidative addition of electron-rich transoid dienes to bromonaphthoquinones
  作者：John R. Grunwell、Anastas Karipides、Carl T. Wigal、Stephen W. Heinzman、John Parlow、Joan A. Surso、Laura Clayton、Fred J. Fleitz、Martin Daffner、Jonathan E. Stevens

  DOI：10.1021/jo00001a020

  日期：1991.1

  This work established the idea that a halogen atom, such as bromine, will act as a control element in the regiospecific formation of a new carbon-carbon bond. The addition of the electron-rich end of a transoid diene to a bromojuglone derivative occurred exclusively at the unsubstituted carbon of the quinone. Thus, 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene (3) and either 2- or 3-bromo-5-hydroxy-1,4-naphthoquinone (1 or 2) afforded the adducts 19 or 20 in 57% or 71% yield. Similarly, 2,2-dimethyl-6-methylene-4-(trimethylsiloxy)-1,3-diox-4-ene (4) and 1 gave 21 in 77% yield.