(cyclopent-3-en-1-ylmethoxy)triisopropylsilane | 171023-18-0

• 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: (cyclopent-3-en-1-ylmethoxy)triisopropylsilane
• 英文别名: 3-cyclopentenemethanol triisopropylsilyl ether；3-((triisopropylsiloxy)methyl)cyclopentene；Cyclopent-3-en-1-ylmethoxy-tri(propan-2-yl)silane
• CAS: 171023-18-0
• 化学式: C₁₅H₃₀OSi
• 分子量: 254.488
• InChiKey: PLCIVDAONAHURO-UHFFFAOYSA-N

物化性质

• 沸点：
  275.5±9.0 °C(Predicted)
• 密度：
  0.863±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  (cyclopent-3-en-1-ylmethoxy)triisopropylsilane 在 碳酸氢钠 、 臭氧 、 三苯基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 36.08h， 生成 N,N'-bis[(1S,2R)-1-(2-bromophenoxy)-1-phenylpropan-2-yl]-N,N'-bis[(2-bromophenyl)methyl]-3-[tri(propan-2-yl)silyloxymethyl]pentane-1,5-diamine
  参考文献：
  名称：

  Syntheses of Stereochemically Diverse Nine-Membered Ring-Containing Biaryls

  摘要：

  A library of nine-membered, biaryl-containing rings has been synthesized in parallel on polystyrene macrobeads. Dimeric medium rings were shown to be accessible via a regio- and stereoselective double cyclization.

  DOI：

  10.1021/ol048273c
• 作为产物：
  描述：

  二烯丙基丙二酸二乙酯 在 吡啶 、 sodium cyanide 、 lithium aluminium tetrahydride 、 trans-dichlorobis(2,6-dibromphenoxy)oxotungsten(VI) 、 四乙基铅 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 26.5h， 生成 (cyclopent-3-en-1-ylmethoxy)triisopropylsilane
  参考文献：
  名称：

  Practical catalyst for cyclic metathesis. Synthesis of functional and/or enantiopure cycloalkenes.

  摘要：

  The oxo-tungsten complex trans-WOCl2(OAr)(2) (Ar = 2,6-dibromophenyl) is prepared by reaction of WOCl4 with 2 equiv of 2,6-dibromophenol. A variety of nonconjugated dienes are cleanly cyclized to the corresponding cycloalkenes using 2 mol % of this catalyst in combination with 4 mol % of tetraethyllead. All three components of the catalyst system are commercially available. The catalytic reactions are typically complete in 1 h at 90 degrees C and allow the synthesis of chiral cycloalkenes with little or no loss in optical activity. For example, (R)- (S)-citronellene have been cyclized to the corresponding (R)- or (S)-3-methylcyclopentenes in 97% enantiomeric excess. The cyclization is compatible with a variety of functional groups including some eater, amide, and ether derivatives. Tri- (but not tetra-) substituted cycloalkenes could be prepared using this catalyst.

  DOI：

  10.1021/ja00140a015

文献信息

• Thioallenoates in catalytic enantioselective [2+2]-cycloadditions with unactivated alkenes
  作者：Michael L. Conner、Johannes M. Wahl、M. Kevin Brown

  DOI：10.1016/j.tet.2019.04.028

  日期：2019.6

  The application of thioallenoates to catalytic enantioselective [2+2]-cycloadditions with unactivated alkenes is reported. In many cases, the thioallenoates examined exhibit superior reactivity and selectivity compared to the allenic esters generally used in these cycloadditions.

  报道了硫代脲基酸酯在具有未活化的烯烃的催化对映选择性[2 + 2]-环加成中的应用。在许多情况下，与通常用于这些环加成中的烯丙酸酯相比，所检测的硫代烯丙酸酯显示出优异的反应性和选择性。
• Practical catalyst for cyclic metathesis. Synthesis of functional and/or enantiopure cycloalkenes.
  作者：William A. Nugent、Jerald Feldman、Joseph C. Calabrese

  DOI：10.1021/ja00140a015

  日期：1995.9

  The oxo-tungsten complex trans-WOCl2(OAr)(2) (Ar = 2,6-dibromophenyl) is prepared by reaction of WOCl4 with 2 equiv of 2,6-dibromophenol. A variety of nonconjugated dienes are cleanly cyclized to the corresponding cycloalkenes using 2 mol % of this catalyst in combination with 4 mol % of tetraethyllead. All three components of the catalyst system are commercially available. The catalytic reactions are typically complete in 1 h at 90 degrees C and allow the synthesis of chiral cycloalkenes with little or no loss in optical activity. For example, (R)- (S)-citronellene have been cyclized to the corresponding (R)- or (S)-3-methylcyclopentenes in 97% enantiomeric excess. The cyclization is compatible with a variety of functional groups including some eater, amide, and ether derivatives. Tri- (but not tetra-) substituted cycloalkenes could be prepared using this catalyst.
• Syntheses of Stereochemically Diverse Nine-Membered Ring-Containing Biaryls
  作者：Shyam Krishnan、Stuart L. Schreiber

  DOI：10.1021/ol048273c

  日期：2004.10.1

  A library of nine-membered, biaryl-containing rings has been synthesized in parallel on polystyrene macrobeads. Dimeric medium rings were shown to be accessible via a regio- and stereoselective double cyclization.