[(2,3-dihydro-1H-inden-2-yl)oxy](1,1-dimethylethyl)dimethylsilane | 216884-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: [(2,3-dihydro-1H-inden-2-yl)oxy](1,1-dimethylethyl)dimethylsilane
• 英文别名: 2-(tert-butyldimethylsiloxy)indane；2-tert-butyldimethylsiloxyindan；2,3-dihydro-2-tert-butyldimethysiloxy-1H-indene；tert-butyl-(2,3-dihydro-1H-inden-2-yloxy)-dimethylsilane
• CAS: 216884-03-6
• 化学式: C₁₅H₂₄OSi
• 分子量: 248.44
• InChiKey: HEMXXNAHJXLYKD-UHFFFAOYSA-N

物化性质

• 沸点：
  286.7±29.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(2,3-dihydro-1H-inden-2-yl)oxy](1,1-dimethylethyl)dimethylsilane 在 bismuth(III) bromide 、 水 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以83%的产率得到2-茚醇
  参考文献：
  名称：

  在芳基叔丁基二甲基甲硅烷基醚存在下，溴化铋对烷基叔丁基二甲基甲硅烷基醚的选择性脱保护

  摘要：

  可以在环境温度下在湿乙腈中使用催化量的溴化铋在芳基醚存在下选择性地裂解烷基叔丁基二甲基甲硅烷基醚。

  DOI：

  10.1016/s0040-4039(00)01012-1
• 作为产物：
  描述：

  tert-Butyl-(3,4-diethynyl-cyclopent-3-enyloxy)-dimethyl-silane 在 正己烷 作用下， 反应 6.0h， 以3%的产率得到[(2,3-dihydro-1H-inden-2-yl)oxy](1,1-dimethylethyl)dimethylsilane
  参考文献：
  名称：

  Photochemical Cycloaromatization of Non-Benzenoid Enediynes

  摘要：

  An efficient photo-Bergman reaction of aliphatic enediynes has been realized. Photolysis of 1 results in the formation of 4 in good yields along with [D2 ]3. Enediyne 4, which has never been isolated in the thermal reaction of 1, arises here by a retro-Bergman reaction of the diradical intermediate 2.

  DOI：

  10.1002/(sici)1521-3773(19990503)38:9<1267::aid-anie1267>3.0.co;2-f

文献信息

• Manganese catalyzed asymmetric oxidation of alkanes to optically active ketones bearing asymmetric center at the α-position
  作者：Naruyoshi Komiya、Satoru Noji、Shun-Ichi Murahashi

  DOI：10.1016/s0040-4039(98)01757-2

  日期：1998.10

  Chiral (salen)manganese(III) complex catalyzed oxidation of symmetrical alkanes with iodosylbenzene gives the corresponding optically active ketones (up to 70% ee). The optically active 2-hydroxy-1-indanone (7) thus obtained is a versatile precursor of cis-1-amino-2-indanol (8) which is a key intermediate of chiral auxiliary and anti HIV protease inhibitor (9).

  手性（salen）锰（III）络合物用碘代苯催化对称烷烃的氧化，得到相应的旋光性酮（ee最高为70％）。由此获得的旋光的2-羟基-1-茚满酮（7）是顺式-1-氨基-2-茚满醇（8）的通用前体，其是手性助剂和抗HIV蛋白酶抑制剂（9）的关键中间体。
• Practical method for hydroxyl-group protection using strontium metal and readily available silyl chlorides
  作者：Norikazu Miyoshi、Aki Miyoshi、Yasuaki Miyazaki、Shigeki Kubo、Masaharu Ueno

  DOI：10.1039/d2cc01105k

  日期：——

  We have found that the etherification of silyl-protected secondary alcohols proceeds smoothly in the presence of strontium metal using silyl chloride instead of the expensive, yet more reactive, and commonly used silyl triflate. The reaction occurred almost completely with various alcohols.

  我们发现，甲硅烷基保护的仲醇的醚化在锶金属存在下使用甲硅烷基氯代替昂贵但更活泼且常用的三氟甲磺酸甲硅烷基酯的情况下顺利进行。用各种醇几乎完全发生反应。
• Manganese-catalyzed enantioselective oxidation of C–H bonds of alkanes and silyl ethers to optically active ketones
  作者：Shun-Ichi Murahashi、Satoru Noji、Tatsuo Hirabayashi、Naruyoshi Komiya

  DOI：10.1016/j.tetasy.2005.08.056

  日期：2005.10

  The (salen)manganese(III) complex-catalyzed oxidation of C-H bonds of symmetrical alkanes and symmetrical 1,3- and 1,4-disilyl ethers with iodosylbenzene gave the corresponding optically active ketones (up to 70% ee) and beta- and gamma-siloxyketones (up to 93% ee). (c) 2005 Elsevier Ltd. All rights reserved.
• In-situ generation of Et3SiBr from BiBr3 and Et3SiH and its use in preparation of dialkyl ethers
  作者：Joginder S. Bajwa、Xinglong Jiang、Joel Slade、Kapa Prasad、Oljan Repič、Thomas J. Blacklock

  DOI：10.1016/s0040-4039(02)01532-0

  日期：2002.9

  The reported BiBr3-Et3SiH catalyzed reductive etherifications of silyl ethers with carbonyl compounds are shown to be catalyzed by the in situ formed Et3SiBr and verified by an independent use of the commercial reagent. As Et3SiBr is moisture sensitive and is not readily available, this in situ generation is still recommended as the method of choice. Utilizing this method, several alcohols were transformed under very mild conditions into dialkyl ethers via their silyl intermediates, such as TES, TBDMS, and TIPS. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 2-(2',2'-DIMETHYLPROPOXY)-2,3-DIHYDRO-1H-INDENE
  作者：Bajwa, Joginder S.、Prasad, Kapa、Repi, Oljan、Holle, Sigrid、Fürstner, Alois

  DOI：10.15227/orgsyn.083.0155

  日期：——