(-)-(S)-3-methylcyclopentene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (-)-(S)-3-methylcyclopentene
• 英文别名: (S)-(-)-3-methylcyclopentene；S-(-)-3-methylcyclopentene；(S)-3-Methylcyclopentene；(3S)-3-methylcyclopentene
• 化学式: C₆H₁₀
• 分子量: 82.1454
• InChiKey: CXOZQHPXKPDQGT-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (-)-(S)-3-methylcyclopentene 、 苯甲腈 N-氧化物 生成 (3aS,6S,6aS)-6-methyl-3-phenyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,2]oxazole
  参考文献：
  名称：

  CURRAN, DENNIS P.;CHOI, SUNG-MO;GOTHE, SCOTT A.;LIN, FU-TYAN, J. ORG. CHEM., 55,(1990) N2, C. 3710-3712

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(+)-溴化香茅酯 在 trans-dichlorobis(2,6-dibromphenoxy)oxotungsten(VI) 、 potassium tert-butylate 、 四乙基铅 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 (-)-(S)-3-methylcyclopentene
  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

• First Direct Synthesis of Optically Active 3-Methylcyclopentene
  作者：Hans-Richard Silwka、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19840670212

  日期：1984.3.14

  (−)-(S)- and (+)-(R)-3-methylcyclopentene (1) has been prepared in a stereochemically unambiguous synthesis. The (S)-configuration for (−)-1 was confirmed by correlation with (−)-(S)-1-methylindane.

  （-）-（S）-和（+）-（R）-3-甲基环戊烯（1）已经通过立体化学明确的合成方法制备。通过与（-）-（S）-1-甲基茚满的相关性确认了（-）- 1的（S）构型。
• CURRAN, DENNIS P.;CHOI, SUNG-MO;GOTHE, SCOTT A.;LIN, FU-TYAN, J. ORG. CHEM., 55,(1990) N2, C. 3710-3712
  作者：CURRAN, DENNIS P.、CHOI, SUNG-MO、GOTHE, SCOTT A.、LIN, FU-TYAN

  DOI：——

  日期：——
• SLIWKA, H. -R.;HANSEN, H. -J., HELV. CHIM. ACTA, 1984, 67, N 2, 434-440
  作者：SLIWKA, H. -R.、HANSEN, H. -J.

  DOI：——

  日期：——
• 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.