12-(tert-butyldimethylsiloxy)-2,2,11,11-tetramethyl-5,8-dioxadodecan-1-ol | 229471-82-3

• 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: 12-(tert-butyldimethylsiloxy)-2,2,11,11-tetramethyl-5,8-dioxadodecan-1-ol
• 英文别名: 4-[2-[4-[Tert-butyl(dimethyl)silyl]oxy-3,3-dimethylbutoxy]ethoxy]-2,2-dimethylbutan-1-ol
• CAS: 229471-82-3
• 化学式: C₂₀H₄₄O₄Si
• 分子量: 376.652
• InChiKey: MOAULAOGNBOCNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-(tert-butyldimethylsiloxy)-2,2,11,11-tetramethyl-5,8-dioxadodecan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.47h， 以90%的产率得到12-(tert-butyldimethylsiloxy)-2,2,11,11-tetramethyl-5,8-dioxadodecan-1-al
  参考文献：
  名称：

  Synthesis and Properties of 7,7,12,12-Tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone

  摘要：

  The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2'-chloroethoxy)ethane, two units derived from isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), 7,7,12,12-tetramethyl-1,4-dioxa-9-cyclotetradecyne-2,8-diol protected by one tetrahydropyran group (15), and 8,11-dihydroxy-7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-9,10-dione (18). X-ray investigation on single crystals of the (R,S) isomer 18a revealed a transannular interaction between the dioxaethane bridge and the dicarbonyl moiety. Calculations (HF/6-31G*) on 4 predict relatively short distances between the oxygen atoms of the dioxyethane bridge and the (CO), part. Investigations by means of cyclic voltammetry, PE and UV/Vis spectroscopy on 4 reveal an interaction between the dioxaethane bridge and the (CO)(4) group.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1303::aid-ejoc1303>3.0.co;2-m
• 作为产物：
  描述：

  2,2,11,11-tetramethyl-5,8-dioxadodecanedioic acid 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 12-(tert-butyldimethylsiloxy)-2,2,11,11-tetramethyl-5,8-dioxadodecan-1-ol
  参考文献：
  名称：

  Synthesis and Properties of 7,7,12,12-Tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone

  摘要：

  The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2'-chloroethoxy)ethane, two units derived from isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), 7,7,12,12-tetramethyl-1,4-dioxa-9-cyclotetradecyne-2,8-diol protected by one tetrahydropyran group (15), and 8,11-dihydroxy-7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-9,10-dione (18). X-ray investigation on single crystals of the (R,S) isomer 18a revealed a transannular interaction between the dioxaethane bridge and the dicarbonyl moiety. Calculations (HF/6-31G*) on 4 predict relatively short distances between the oxygen atoms of the dioxyethane bridge and the (CO), part. Investigations by means of cyclic voltammetry, PE and UV/Vis spectroscopy on 4 reveal an interaction between the dioxaethane bridge and the (CO)(4) group.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1303::aid-ejoc1303>3.0.co;2-m

文献信息

• Synthesis and Properties of 7,7,12,12-Tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone
  作者：Christoph Braunweiler、Sabine Bethke、Frank Rominger、Rolf Gleiter

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1303::aid-ejoc1303>3.0.co;2-m

  日期：1999.6

  The fourteen-membered ring of 7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-8,9,10,11-tetrone (4) was built up from 1,2-bis(2'-chloroethoxy)ethane, two units derived from isobutyric acid and acetylene. Key intermediates were 2,2,11,11-tetramethyl-5,8-dioxadodecane-1,12-diol (8), 7,7,12,12-tetramethyl-1,4-dioxa-9-cyclotetradecyne-2,8-diol protected by one tetrahydropyran group (15), and 8,11-dihydroxy-7,7,12,12-tetramethyl-1,4-dioxacyclotetradecane-9,10-dione (18). X-ray investigation on single crystals of the (R,S) isomer 18a revealed a transannular interaction between the dioxaethane bridge and the dicarbonyl moiety. Calculations (HF/6-31G*) on 4 predict relatively short distances between the oxygen atoms of the dioxyethane bridge and the (CO), part. Investigations by means of cyclic voltammetry, PE and UV/Vis spectroscopy on 4 reveal an interaction between the dioxaethane bridge and the (CO)(4) group.