1,7,7-trimethyl-3-(1-phenylmethylidene)bicyclo[2.2.1]heptan-2-one | 36065-09-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,7,7-trimethyl-3-(1-phenylmethylidene)bicyclo[2.2.1]heptan-2-one
• 英文别名: 3-benzylidene bornanone；3-benzylidenecamphor；3-Benzyliden-(+)-campher；(1R,4S)-1,7,7-Trimethyl-3-(phenylmethylene)bicyclo[2.2.1]heptan-2-one；(1R,4S)-3-benzylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 36065-09-5
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: OIQXFRANQVWXJF-PBHICJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,7,7-trimethyl-3-(1-phenylmethylidene)bicyclo[2.2.1]heptan-2-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 (1R,4R)-exo-3-benzyl-exo-1,7,7-trimethyl-bicyclo<2.2.1>heptan-2-ol
  参考文献：
  名称：

  八分法则规则1：XXIII。γ，δ-不饱和酮中的抗辛酸作用。

  摘要：

  的和α -苄基的（分别为1和2）的衍生物（+） -樟脑已被合成并发现施加在圆二色性Ñ→π有很强的影响*棉效果：1：Δε 301最大-0.36（正-庚烷）和2：相对于樟脑：Δϵ 302 max +3.22：Δϵ 304 max +1.8（正庚烷）。在n→π * UV中发现了这些γ，δ-不饱和系统中电偶极跃迁耦合的证据：UV：1：ϵ 291 max 84（正庚烷）和2：ϵ 285 max 303，相对于樟脑：290 290最多25个。

  DOI：

  10.1016/s0040-4020(01)87782-6
• 作为产物：
  描述：

  (+)-(E)-3-(α-chlorobenzylidene)camphor 在 白樟油 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1,7,7-trimethyl-3-(1-phenylmethylidene)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Synthesis of the first C2-asymmetric phosphinine and its pyrylium precursor

  摘要：

  The synthesis of the first C-2 chiral phosphinine (phosphabenzene) and its pyrylium salt precursor is reported. The chiral phosphinine is derived from (+)-camphor, is a crystalline air-stable solid and is shown to effectively form complexes with metals. A preliminary result using the phosphinine as a ligand for asymmetric catalysis is reported and rationalized structurally. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.085

文献信息

• RuCl2(DMSO)4 catalyzes the β-alkylation of secondary alcohols with primary alcohols through a hydrogen autotransfer process
  作者：Ricardo Martínez、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tet.2006.07.012

  日期：2006.9

  The electrophilic beta-alkylation of secondary alcohols with primary alcohols is accomplished by a hydrogen autotransfer process catalyzed by RUCl2(DMSO)(4). The reaction can produce either simple alkylated secondary alcohols or alpha,beta-unsaturated ketones with good to excellent results just by choosing the appropriate starting secondary alcohol (methyl or longer chain secondary alcohol, respectively), as well as quinolines (by using 2-aminobenzyl alcohol). (c) 2006 Elsevier Ltd. All rights reserved.
• Schenone; Minardi; Bignardi, Farmaco, Edizione Scientifica, 1968, vol. 23, # 10, p. 983 - 993
  作者：Schenone、Minardi、Bignardi

  DOI：——

  日期：——
• The octant rule11For part 22 see D.A. Lightner, T.D. Bouman, B.V. Crist, S.L. Rodgers, M.A. Knobeloch and A.M. Jones, J. Am. Chem. Soc., in press (1987).
  作者：Vien Van Toan、David A. Lightner

  DOI：10.1016/s0040-4020(01)87782-6

  日期：——

  The and α-benzyl derivatives (1 and 2, respectively) of (+)-camphor have been synthesized and are found to exert a strong influence on the circular dichroism n→π* Cotton effects: 1: Δϵ301max -0.36 (n- heptane) and 2: Δϵ302max +3.22, relative to camphor: Δϵ304max +1.8 (n-heptane). Evidence for electric dipole transition moment coupling in these γ, δ -unsaturated systems is found in the n→π* UV: 1: ϵ291max

  的和α -苄基的（分别为1和2）的衍生物（+） -樟脑已被合成并发现施加在圆二色性Ñ→π有很强的影响*棉效果：1：Δε 301最大-0.36（正-庚烷）和2：相对于樟脑：Δϵ 302 max +3.22：Δϵ 304 max +1.8（正庚烷）。在n→π * UV中发现了这些γ，δ-不饱和系统中电偶极跃迁耦合的证据：UV：1：ϵ 291 max 84（正庚烷）和2：ϵ 285 max 303，相对于樟脑：290 290最多25个。
• Synthesis of the first C2-asymmetric phosphinine and its pyrylium precursor
  作者：Jason R. Bell、Andreas Franken、Charles M. Garner

  DOI：10.1016/j.tet.2009.08.085

  日期：2009.11

  The synthesis of the first C-2 chiral phosphinine (phosphabenzene) and its pyrylium salt precursor is reported. The chiral phosphinine is derived from (+)-camphor, is a crystalline air-stable solid and is shown to effectively form complexes with metals. A preliminary result using the phosphinine as a ligand for asymmetric catalysis is reported and rationalized structurally. (c) 2009 Elsevier Ltd. All rights reserved.