1-羟基-6,6-二甲基-2-庚烯-4-炔 | 173200-56-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-羟基-6,6-二甲基-2-庚烯-4-炔
• 英文名称: (E)-6,6-dimethylhept-2-en-4-yn-1-ol
• 英文别名: (E)-6,6-dimethylhept-2-ene-4-ynol；6,6-dimethyl-2-hepten-4-yn-1-ol；1-Hydroxy-6,6-dimethyl-2-heptene-4-yne
• CAS: 173200-56-1
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: GALYLLJOCKLAGD-GQCTYLIASA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  1-羟基-6,6-二甲基-2-庚烯-4-炔 在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 特比萘芬杂质5
  参考文献：
  名称：

  通过有机铜与乙酰烯基迈克尔受体的共轭1,6-，1,8-，1,10-和1,12加成反应合成乙烯基烯丙二烯及其在分子间Diels-Alder反应中用作二烯

  摘要：

  通过共轭铜酸酯加成到炔属迈克尔受体上，合成了各种乙烯基烯丙二烯。因此，分别与2-en-4-酸酯1、3和5a进行1,6-加成反应后，形成区域的烯丙基烯醇盐进行了区域选择性亲电捕获，从而得到了乙烯基亚烷基2、4和7。同样地，向2,4-二烯-6-壬酸酯8a和10加成1,8 ，得到乙烯基烯丙基9和11，而向2,4,6-三烯-8-壬酸酯中加成Me 2 CuLi的1,10。图12提供了丙二烯13，以及向2,4,6,8-四烯基-10ynoate 14的类似的1,12加成。装备了多烯15。这些乙烯基丙二烯在区域和立体选择性Diels-Alder反应中是有价值的亲二烯体，如环加成产物16-24的形成所证明。在路易斯酸的存在下，乙烯基亚丙基4a大概重排为环戊二烯衍生物，其随后形成环加合物25和26。

  DOI：

  10.1002/jlac.199619961002
• 作为产物：
  描述：

  ethyl 6,6-dimethyl-2-hepten-4-ynoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-羟基-6,6-二甲基-2-庚烯-4-炔
  参考文献：
  名称：

  共轭烯炔醇/胺的化学，区域和立体选择性氢硼化：带有羟基/氨基的Z，Z- / Z，E -1,3-dien-1 / 2-基硼酸酯的轻松合成

  摘要：

  分别以铜盐和双（频哪醇）二硼为预催化剂和硼源研究了共轭烯炔醇/胺的硼氢化反应。建议化学选择性源自基质上杂原子和过渡金属上配体的综合电子影响。区域选择性可能主要由炔烃取代基的电子效应决定。这项研究导致了访问带有羟基/氨基的Z，Z- / Z，E -1,3-dien-1 / 2-ylboronic酯的高选择性方案。

  DOI：

  10.1016/j.tetlet.2016.05.075

文献信息

• Antifungal derivatives of
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04751245A1

  公开（公告）日：1988-06-14

  N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine derivatives are provided having the general formula ##STR1## wherein R.sub.1 is methoxy, iminomethyl or 1-iminoethyl and R.sub.2 and R.sub.3 are each hydrogen; or R.sub.1 is methyl and one of R.sub.2 and R.sub.3 is hydrogen and the other is halogen. The above compounds as well as acid-addition salts thereof are useful as antifungal agents.

  提供具有一般式##STR1##的N-(6,6-二甲基-2-庚烯-4-炔基)-1-萘甲胺衍生物，其中R.sub.1是甲氧基、亚胺甲基或1-亚胺乙基，R.sub.2和R.sub.3分别是氢；或者R.sub.1是甲基，R.sub.2和R.sub.3中的一个是氢，另一个是卤素。上述化合物及其酸盐加合物可用作抗真菌剂。
• PREPARATION AND UTILITY OF SUBSTITUTED ALLYLAMINES
  申请人：Gant Thomas G.

  公开号：US20080167312A1

  公开（公告）日：2008-07-10

  Disclosed herein are substituted allylamines having structural Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and the methods of their use thereof.

  本文公开了具有结构式I的取代烯丙胺，其制备过程，制药组合物以及使用方法。
• Antifungal derivatives of N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine and method of using same
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0251574A2

  公开（公告）日：1988-01-07

  N-(6,6-dimethyl-2-hepten-4-ynyl)-1-­naphthalenemethanamine derivatives are provided having the general formula wherein R₁ is methoxy, iminomethyl or 1-iminoethyl and R₂ and R₃ are each hydrogen; or R₁ is methyl and one of R₂ and R₃ is hydrogen and the other is halogen. The above compounds as well as acid-addition salts thereof are useful as antifungal agents.

  提供了具有通式的 N-(6,6-二甲基-2-庚烯-4-炔基)-1-萘甲胺衍生物，其中 R₁ 为甲氧基、亚氨基甲基或 1-亚氨基乙基，R₂ 和 R₃ 均为氢；或 R₁ 为甲基，R₂ 和 R₃ 中的一个为氢，另一个为卤素。 上述化合物及其酸加成盐可用作抗真菌剂。
• Identification of a Reactive Metabolite of Terbinafine:  Insights into Terbinafine-Induced Hepatotoxicity
  作者：Suzanne L. Iverson、Jack P. Uetrecht

  DOI：10.1021/tx0002029

  日期：2001.2.1

  Oral terbinafine treatment for superficial fungal infections of toe and fingernails is associated with a low incidence (1:45000) of hepatobiliary dysfunction. Due to the rare and unpredictable nature of this adverse drug reaction, the mechanism of toxicity has been hypothesized to be either an uncommon immunological or metabolically mediated effect. However, there is little evidence to support either mechanism, and toxic metabolites of terbinafine have not been identified. We incubated terbinafine with both rat and human liver microsomal protein in the presence of GSH and were able to trap an allylic aldehyde, 7,7-dimethylhept-2-ene-4-ynal (TBFA), which corresponds to the N-dealkylation product of terbinafine. TBF-A was also prepared synthetically and reacted with excess GSH to yield conjugates with HPLC retention times and mass spectra identical to those generated in the microsomal incubations. The major GSH conjugate, characterized by H-1 NMR, corresponds to addition of GSH in a 1,6-Michael fashion. There remains a second electrophilic site on this metabolite, which can bind either to a second molecule of GSH or to cellular proteins via a 1,4-Michael addition mechanism. Moreover, we demonstrated that the formation of the GSH conjugates was reversible. We speculate that this allylic aldehyde metabolite, formed by liver enzymes and conjugated with GSH, would be transported across the canalicular membrane of hepatocytes and concentrated in the bile. The mono-GSH conjugate, which is still reactive, could bind to hepatobiliary proteins and lead to direct toxicity. Alternatively, it could modify canalicular proteins and lead to an immune-mediated reaction causing cholestatic dysfunction.
• US4751245A
  申请人：——

  公开号：US4751245A

  公开（公告）日：1988-06-14