(E)-1-phenyl-1-decen-3-ol | 124745-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1-phenyl-1-decen-3-ol
• 英文别名: (1E)-phenyldec-1-en-3-ol；(E)-1-phenyldec-1-en-3-ol
• CAS: 124745-48-8
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: UTSXNXMVYSNVLL-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-(氯硫基)吗啉 、 (E)-1-phenyl-1-decen-3-ol 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以75%的产率得到(E)-4-<(1-phenyldec-2-enyl)sulfinyl>morpholine
  参考文献：
  名称：

  4-（2'-烯烃亚砜基）-吗啉的锂化和烷基化，这是取代烯丙基亚磺酰胺的简单途径

  摘要：

  通过在三乙胺的存在下与4-吗啉磺酰氯反应，几种取代的烯丙基醇已被转化为相应的烯丙基亚磺酰胺。作为一种补充方法，已经制备了新的硫代衍生物II，并用有机卤化物有效地烷基化了。

  DOI：

  10.1016/s0040-4039(00)99625-4
• 作为产物：
  描述：

  trans-1-phenyl-1-decen-3-one 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 3.0h， 以90%的产率得到(E)-1-phenyl-1-decen-3-ol
  参考文献：
  名称：

  Evaluation of the antitrypanosoma activity and SAR study of novel LINS03 derivatives

  摘要：

  Chagas' disease is a parasitic infection caused by Trypanosoma cruzi that is still treated by old and toxic drugs. In the search for novel alternatives, natural sources are an important source for new drug prototypes against T. cruzi to further structural exploitation. A set of natural-based compounds (LINS03) was designed, showing promising antitrypanosoma activity and low cytotoxicity to host cells. In this paper, nine novel LINS03 derivatives were evaluated against T. cruzi trypomastigotes and amastigotes. The selectivity was assessed through cytotoxicity assays using NCTC mammalian cells and calculating the CC50/IC50 ratio. The results showed that compounds 2d and 4c are noteworthy, due their high activity against amastigotes (IC50 13.9 and 5.8 mu M) and low cytotoxicity (CC50 107.7 mu M and > 200 mu M, respectively). These compounds did not showed alteration on plasma membrane permeability in a Sytox green model. SAR analysis suggested an ideal balance between hydrosolubility and lipophilicity is necessary to improve the activity, and that insertion of a meta-substituent is detrimental to the activity of the amine derivatives but not to the neutral derivatives, suggesting different mechanisms of actions. The results presented herein are valuable for designing novel compounds with improved activity and selectivity to be applied in future studies.

  DOI：

  10.1016/j.bioorg.2019.102996

文献信息

• Highly Selective Catalytic Intermolecular Reductive Coupling of Alkynes and Aldehydes
  作者：Wei-Sheng Huang、Johann Chan、Timothy F. Jamison

  DOI：10.1021/ol006781q

  日期：2000.12.1

  Alkynes (internal and terminal) and aldehydes (aromatic and aliphatic) are reductively coupled in a single catalytic reaction to yield di- and trisubstituted allylic alcohols with high stereoselectivity and regioselectivity. In most cases, a 1:1 ratio of alkyne to aldehyde is sufficient for efficient coupling. The yield and regioselectivity are strongly dependent on the phosphine ligand, but the allylic

  炔烃（内部和末端）和醛（芳香族和脂肪族）在单个催化反应中还原偶联，生成具有高立体选择性和区域选择性的二取代和三取代的烯丙醇。在大多数情况下，炔烃与醛的1：1比例足以有效偶联。产率和区域选择性强烈地取决于膦配体，但是形成的烯丙基醇始终是顺式加成至炔烃的产物。
• Baudin, Jean-Bernard; Julia, Sylvestre, Bulletin de la Societe Chimique de France, 1995, vol. 132, # 2, p. 196 - 214
  作者：Baudin, Jean-Bernard、Julia, Sylvestre

  DOI：——

  日期：——
• BOUDIN, JEAN-BERNARD;JULIA, SYLVESTRE A., TETRAHEDRON LETT., 30,(1989) N5, C. 1963-1989
  作者：BOUDIN, JEAN-BERNARD、JULIA, SYLVESTRE A.

  DOI：——

  日期：——