11-phenylundec-10-en-1-ol | 194865-40-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-phenylundec-10-en-1-ol
• 英文别名: (E)-11-phenylundec-10-en-1-ol
• CAS: 194865-40-2
• 化学式: C₁₇H₂₆O
• 分子量: 246.393
• InChiKey: BZUGKPGWXBYSCP-UKTHLTGXSA-N

物化性质

• 熔点：
  35-37 °C
• 沸点：
  369.9±11.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-phenylundec-10-en-1-ol 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 11-phenylundecan-1-ol
  参考文献：
  名称：

  Surinone B，alatanones AB和trineurone A的总合成。

  摘要：

  四个聚酮化合物，surinone B（全合成1），alatanones A-B（2 - 3），和trineurone A（4）经一锅C-酰化反应通过耦合的有效和统一的策略完成1,3-环己二酮与EDC活化的酸在温和的条件下。发现Alatanone A（2）是一种有效的抗革兰氏阳性和革兰氏阴性细菌的抗菌剂，MIC为31.25μg/ ml，而Alatanone B（3）被发现是一种有效的抗Cladosporium cladosporioides的抗真菌剂。MIC为62.5μg/ ml，而环己酰亚胺MIC为125μg/ ml。我们的方法可以对这些稀有的聚酮化合物进行千克规模的分析，以开发新的抗菌剂。

  DOI：

  10.1080/10286020.2018.1460362
• 作为产物：
  描述：

  10-十一烯醛 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 磷酸 、 双氧水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 47.5h， 生成 11-phenylundec-10-en-1-ol
  参考文献：
  名称：

  Palladium-Catalyzed Isomerization of Aryl-Substituted Epoxides:  A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones

  摘要：

  Aryl-substituted epoxides bearing multiple methyl substituents on the epoxide ring isomerize in the presence of 5 mol % Pd(OAc)(2)PR3 (R = n-Bu, Ph) to form the corresponding benzylic aldehyde or ketone, with complete regioselectivity for the carbonyl compound formed via cleavage of the benzylic C-O bond. No allylic alcohols or products arising from alkyl migration are observed. Rapid reaction rates and nearly quantitative yields are obtained, even with highly sterically hindered epoxides, using tri-n-butylphosphine as ligand and tert-butyl alcohol as solvent. 2-Aryl-substituted epoxides with two methyl substituents on C3 are completely unreactive, consistent with an oxidative addition/beta-hydride elimination mechanism. Catalyst variation studies show that both Pd(OAc)(2) and PR3 are essential for optimal activity and that palladium catalysts formed in this manner are superior to other Pd(O) catalysts (e.g., Pd(PPh3)(4)). The reactivity of catalytic Pd(OAc)(2)/PR3 toward multiply-substituted epoxides is compared to traditional Lewis acid catalysts; the former is found to be much more selective for isomerization without skeletal rearrangement. A mechanistic rationale involving turnover-limiting S(N)2-like attack of Pd(O) at the benzylic carbon is proposed.

  DOI：

  10.1021/jo970743b

文献信息

• Operationally Simple and Highly (<i>E</i>)-Styrenyl-Selective Heck Reactions of Electronically Nonbiased Olefins
  作者：Erik W. Werner、Matthew S. Sigman

  DOI：10.1021/ja203164p

  日期：2011.6.29

  Simple, mild, and efficient conditions are reported for a Pd(0)-catalyzed Heck reaction that delivers high yields and selectivity for (E)-styrenyl products using electronically nonbiased olefin substrates bearing a range of useful functionality. Preliminary mechanistic studies demonstrate that the σ-donating DMA solvent is crucial for high selectivity. Further studies suggest that the catalyst distinguishes

  据报道，Pd(0) 催化的 Heck 反应采用简单、温和且有效的条件，该反应使用带有一系列有用功能的电子无偏烯烃底物，为 (E)-苯乙烯基产物提供高产率和选择性。初步机理研究表明，σ 供体 DMA 溶剂对于高选择性至关重要。进一步的研究表明，与之前报道的 Pd(II) 催化氧化反应条件相比，该催化剂根据它们的相对氢化特性来区分 β-氢。
• Copper(0) nanoparticle catalyzed <i>Z</i> ‐Selective Transfer Semihydrogenation of Internal Alkynes
  作者：Maria Jesus Moran、Katia Martina、Vidmantas Bieliunas、Francesca Baricco、Silvia Tagliapietra、Gloria Berlier、Wim M. De Borggraeve、Giancarlo Cravotto

  DOI：10.1002/adsc.202100126

  日期：2021.6.8

  The use of copper(0) nanoparticles in the transfer semihydrogenation of alkynes has been investigated as a lead-free alternative to Lindlar catalysts. A stereo-selective methodology for the hydrogenation of internal alkynes to the corresponding (Z)-alkenes in high isolated yields (86% average) has been developed. This green and sustainable transfer hydrogenation protocol relies on non-noble copper

  已经研究了在炔烃转移半氢化中使用铜 (0) 纳米粒子作为 Lindlar 催化剂的无铅替代品。一种将内炔氢化成相应的 ( Z) 的立体选择性方法)-烯烃的高分离产率（平均 86%）已被开发出来。这种绿色且可持续的转移氢化协议依赖于非贵重铜纳米粒子来还原富电子和缺电子、脂肪族取代和芳香族取代的内部炔烃。多元醇，如乙二醇和甘油，已被证明可作为氢源，并观察到优异的立体选择性和化学选择性。无论是单独使用还是组合使用，微波和超声波辐射等辅助技术都可以增强传热和传质，从而将反应时间从几小时缩短到几分钟。
• A Highly Selective and General Palladium Catalyst for the Oxidative Heck Reaction of Electronically Nonbiased Olefins
  作者：Erik W. Werner、Matthew S. Sigman

  DOI：10.1021/ja1060998

  日期：2010.10.13

  A general, highly selective oxidative Heck reaction is reported. The reaction is high-yielding under mild conditions without the need for base or high temperatures, and the selectivity is excellent, without the requirement for electronically biased olefins or other specific directing groups. A preliminary mechanistic investigation suggests that the unusually high selectivity may be due to the catalyst's sensitivity to C-H bond strength in the selectivity-determining beta-hydride elimination step.
• LAROCK, RICHARD C.;LAUND, WAI-YEE;STOLZ-DUNN, SANDRA, TETRAHEDRON LETT., 30,(1989) N8, C. 6629-6632
  作者：LAROCK, RICHARD C.、LAUND, WAI-YEE、STOLZ-DUNN, SANDRA

  DOI：——

  日期：——
• SMALL CELL FOAMS AND BLENDS AND A PROCESS FOR THEIR PREPARATION
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0680498A1

  公开（公告）日：1995-11-08