1-bromo-6,6-dimethyl-2-hepten-4-yne | 126764-15-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1-bromo-6,6-dimethyl-2-hepten-4-yne
• 英文别名: 1-Bromo-6,6-dimethylhept-2-en-4-yne
• CAS: 126764-15-6
• 化学式: C₉H₁₃Br
• mdl: MFCD09263751
• 分子量: 201.106
• InChiKey: OOLYZFSILFGXCC-UHFFFAOYSA-N

物化性质

• 沸点：
  65°C 20mm
• 密度：
  1,12 g/cm3
• 闪点：
  14°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 安全说明：
  S16,S26,S36/37/39
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1993

反应信息

• 作为反应物：
  描述：

  1-bromo-6,6-dimethyl-2-hepten-4-yne 在 sodium tetrahydroborate 、 TEA 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (Z)-N,6,6-trimethyl-2-hepten-4-yn-1-amine
  参考文献：
  名称：

  Highly selective TFAA-cleavage of tertiary 2,4-dimethoxybenzylamines and its use in the synthesis of secondary amines

  摘要：

  TFAA-treatment of allylic, propargylic, homopropargylic and some benzylic tert. 2,4-dimethoxybenzylamines leads to highly selective cleavage of their dimethoxybenzylic C-N bonds. The resultant trifluoroacetamides can then readily be converted to the corresponding secondary amines.

  DOI：

  10.1016/s0040-4020(01)86465-6
• 作为产物：
  描述：

  3-羟基-6,6-二甲基-1-庚烯-4-炔 在 氢溴酸 、 三溴化磷 作用下， 以 乙醇 为溶剂， 以97.12%的产率得到1-bromo-6,6-dimethyl-2-hepten-4-yne
  参考文献：
  名称：

  一种盐酸特比萘芬Z型异构体的制备方法

  摘要：

  本发明公开了一种盐酸特比萘芬Z型异构体的制备方法，所述的方法以叔丁基乙炔为起始物料，经正丁基锂反应转化为3,3‑二甲基‑1‑丁炔基锂，与丙烯醛合成中间体13‑羟基‑6,6‑二甲基‑1‑庚烯‑4‑炔，再经过卤代合成中间体2E/Z‑1‑溴‑6,6‑二甲基‑2‑庚烯‑4‑炔；上述中间体2与N‑甲基‑1‑萘甲胺在碱性条件下缩合成特比萘芬游离碱，再用氯化氢成盐、用甲基叔丁基醚精制，得到高纯度盐酸特比萘芬异构体(Z)‑N‑(6,6‑二甲基庚‑2‑烯‑4‑炔基)‑N‑甲基‑1‑萘甲胺。本发明工艺路线简短，合成步骤相对简单，实验所用原料易得，反应条件比较温和，产品质量稳定，全程操作简单易实施，制备样品纯度较高，可用于特比萘芬Z型异构体对照品的制备。

  公开号：

  CN115073303A

文献信息

• Structure Activity Relationships of New Inhibitors of Mammalian 2,3-Oxidosqualene Cyclase Designed from Isoquinoline Derivatives.
  作者：Jean Binet、Didier Thomas、Abdellah Benmbarek、Daniel de Fornel、Patrice Renaut

  DOI：10.1248/cpb.50.316

  日期：——

  We have designed more potent inhibitors from the previously reported LF 05-0038, a 6-isoquinolinol based inhibitor of 2,3-oxidosqualene cyclase (IC50: 1.1 μM). Replacement of the 3-OH group by various 3-substituted amino groups, and modification of the alkyl chain borne by the endocyclic nitrogen led to inhibitors with IC50 in the range of 0.15 to 1 μM. In a second step, opening of the bicyclic ring system afforded the corresponding aminoalkylpiperidines which were slightly more potent. Finally, introduction of suitable aromatic containing moieties on the piperidine nitrogen yielded very potent inhibitors such as 20x (IC50=18 nM) easy to synthesize and achiral. The recent availability of the crystal structure of squalene-hopene cyclase allowed us to construct a three-dimensional (3D) model of the related 2,3-oxidosqualene cyclase (OSC) which was tentatively used to describe the possible mode of binding of our compounds and which can be useful for designing new inhibitors.

  我们从之前报告的LF 05-0038（一种基于6-异喹啉醇的2,3-氧化甾烯环化酶抑制剂，IC50：1.1 μM）中设计了更有效的抑制剂。通过用各种3-取代氨基取代3-OH基团，以及修饰内环氮原子所带的烷基链，获得了IC50在0.15到1 μM范围的抑制剂。在第二步中，打开双环系统得到相应的氨基烷基哌啶，这些化合物的活性稍强。最后，在哌啶氮上引入合适的含芳香族基团，得到了很强的抑制剂，例如20x（IC50=18 nM），其合成简单且不具有手性。近期可获得的甾烯-霍彭环化酶的晶体结构，使我们得以构建相关的2,3-氧化甾烯环化酶（OSC）的三维（3D）模型，并初步用于描述我们的化合物可能的结合模式，这对设计新抑制剂是非常有用的。
• Benzopyrane and benzothiopyrane derivatives useful as anti-mycotic agents
  申请人：Sandoz Ltd.

  公开号：US04382951A1

  公开（公告）日：1983-05-10

  Benzopyrane and benzothiopyrane derivatives which possess pharmaceutical in particular anti-mycotic activity.

  苯并吡喃和苯并噻吩衍生物具有药物特性，特别是抗真菌活性。
• Derivatives of .beta., .beta.-dimethyl-4-piperidineethanamine as
  申请人：Fournier Industrie et Sante

  公开号：US05614534A1

  公开（公告）日：1997-03-25

  The present invention concerns .beta.,.beta.-dimethyl-4-piperidineethanamine compounds of the formula: ##STR1## (wherein groups R.sub.1 to R.sub.3 are defined as indicated in the description), and addition salts thereof. It also concerns a process for their preparation and their therapeutic use as inhibitors for the cholesterol biosynthesis, in particular as epoxysqualene cyclase inhibitors, for obtaining an as hypocholesterolemic, hypolipemic, antiatheromatic and/or antifungal drug.

  本发明涉及公式为：##STR1##（其中，基团R.sub.1到R.sub.3如说明书中所示定义）和其盐的.beta.，.beta.-二甲基-4-哌啶乙胺化合物。还涉及一种制备它们的方法以及它们作为胆固醇生物合成抑制剂的治疗用途，特别是作为环氧角鲨烯环化酶抑制剂，以获得降低胆固醇、降低血脂、抗动脉粥样硬化和/或抗真菌药物。
• Process for the preparation of 6,6-dimethylhept-1-en-4-yn-3-ol
  申请人：——

  公开号：US20020016517A1

  公开（公告）日：2002-02-07

  The invention provides a process for the preparation of 6,6-dimethylhept-1-en-4-yn-3-ol comprising of reacting t-butylacetylene with a proton-extracting agent selected from the group consisting of an organometallic compound and metallic lithium to form a t-butylacetylide, reacting the acetylide with acrolein at temperatures between −40° C. to +20° C., quenching the reaction mixture and isolating the product.

  这项发明提供了一种制备6,6-二甲基庚-1-烯-4-炔-3-醇的方法，包括将叔丁基乙炔与从有机金属化合物和金属锂组成的质子提取剂中选择的一种反应，形成叔丁基乙炔基，将乙炔基与丙烯醛在-40℃至+20℃的温度范围内反应，淬灭反应混合物并分离产物。
• Substituted alkylamine derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05234946A1

  公开（公告）日：1993-08-10

  The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7, X and Y are linking groups, R.sup.2 is H or lower alkyl, R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl, R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms, R.sup.6 represents (a) substituted or unsubstituted acyclic hydrocarbon group which may be unsaturated, (b) substituted or unsubstituted cycloalkyl group, or (c) substituted or unsubstituted phenyl group, or non-toxic salts thereof. (E)-N-(6-6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[4-(3-thienyl)-2-thienyl-me thyloxy]benzylamine hydrochloride is a representative example. The substituted alkylamine derivatives are useful as pharmaceuticals, particularly for the treatment and prevention of hypercholesterolemia, hyperlipemia and arteriosclerosis.

  公式（I）所代表的取代基烷基胺衍生物，其中R1代表（a）取代或未取代的C2-6烯丙基基团，（b）取代或未取代的C3-6环烯基基团，（c）取代或未取代的C2-6炔基基团，（d）取代或未取代的芳基基团，（e）取代或未取代的杂环基团，（f）可能被取代的融合杂环基团，或（g）由Ru11-Ar表示的基团，其中R11是杂环基团，Ar是5-或6-成员芳香环，可以含有杂原子N、O或S，且可以被取代；表示5-或6-成员芳香环，可以含有杂原子N、O或S，可以被R7取代，X和Y是连接基团，R2是H或较低的烷基，R3是氢、较低的烷基、较低的烯丙基、较低的炔基或较低的环烷基，R4和R5独立地表示氢或卤素原子，R6表示（a）取代或未取代的非环烷基，可以不饱和，（b）取代或未取代的环烷基，或（c）取代或未取代的苯基，或其非毒性盐。 （E）-N-（6-6-二甲基-2-庚烯-4-炔基）-N-乙基-3- [4-（3-噻吩基）-2-噻吩基]甲氧基]苯基胺盐酸盐是一个代表性的例子。这些取代基烷基胺衍生物可用作药物，特别是用于治疗和预防高胆固醇血症、高脂血症和动脉硬化。