5-heptyne-2-ol | 103583-64-8

• 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: 5-heptyne-2-ol
• 英文别名: hept-5-yn-2-ol
• CAS: 103583-64-8
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: GDTBEBCJWDXQIF-UHFFFAOYSA-N

物化性质

• 熔点：
  -20.62°C (estimate)
• 沸点：
  180.13°C (rough estimate)
• 密度：
  0.8469 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  5-heptyne-2-ol 在 Pd₂(dba)3*HCl 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (Z)-6-phenyl-5-hepten-1-ol
  参考文献：
  名称：

  Intramolecular Endo-Dig Hydrosilylation Catalyzed by Ruthenium:  Evidence for a New Mechanistic Pathway

  摘要：

  The ruthenium catalyst [Cp*Ru(MeCN)3]PF6 effects a novel intramolecular hydrosilylation of homo- and bis-homopropargylic alcohols, producing products of unique regioselectivity under very mild conditions with excellent selectivity. The reaction is compatible with a wide range of functional groups and tolerates substantial steric bulk. In addition to producing valuable synthetic intermediates thus far obtainable only in circuitous fashion, the results imply the necessity for a reexamination of the mechanism surrounding trans-hydrosilylation reactions, at least for ruthenium catalysts. At the very least, a simple cis addition/isomerization mechanism almost certainly cannot be active in this case. A silicon-ruthenium transposition could potentially provide a rationalization. However, the evidence for any products of syn addition with nonhydrido ruthenium catalysts is very scarce. Alternatively, a direct trans addition to orthogonal p-systems is also a possibility.

  DOI：

  10.1021/ja028766h
• 作为产物：
  描述：

  2-(but-3'-ynyl)-2-methyl-1,3-dioxolane 在 盐酸 、 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 水 为溶剂， 反应 19.0h， 生成 5-heptyne-2-ol
  参考文献：
  名称：

  分子内环加成法合成（±）-肌act啶

  摘要：

  描述了一种新的（±）-act啶（1）合成，该合成依赖于乙炔在嘧啶环上的分子内环加成。制备5-（庚基-5-yn-2-基）-4，6-二羟基嘧啶（2），然后热解，得到1-羟基act啶（13），可以通过氯化和氢化将其转化为（±）-act啶。

  DOI：

  10.1039/p19810001909

文献信息

• Method of preparation of an alkyne with an optically active hydroxyl group in the beta or gamma position of a triple bond and intermediates obtained
  申请人：Garel Laurent

  公开号：US20070004942A1

  公开（公告）日：2007-01-04

  The present invention relates to a method of preparation of an alkyne with an optically active hydroxyl group in the β or γ position of a triple bond and intermediates obtained. The method of the invention for preparation of an alkyne with an optically active hydroxyl group in the β position of a triple bond is characterized in that it comprises the reaction, in the presence of a Lewis acid: of a compound of formula (IV): in which: R is a linear or branched alkyl group having from 1 to 6 carbon atoms. and of a compound of formula (V): R′—C≡C-M   (V) in which: R′ represents a hydrogen atom, a linear or branched alkyl group having from 1 to 8 carbon atoms, preferably a methyl group or a trialkylsilyl group. M represents a metal, preferably a metal of group (Ia) of the periodic table, preferably lithium. Another object of the invention comprises the production of an alkyne with an optically active hydroxyl group in the γ position of a triple bond by isomerization of an alkyne with an optically active hydroxyl group in the β position previously obtained.

  本发明涉及一种制备具有β或γ位置上的光学活性羟基的炔烃的方法及其中间体的制备。用于制备具有β位置上的光学活性羟基的炔烃的本发明方法的特征在于它包括在Lewis酸存在下的反应：化合物的化合物（IV）：其中：R是具有1至6个碳原子的直链或支链烷基基团。和化合物的化合物（V）：R′—C≡C-M （V）其中：R′代表氢原子，具有1至8个碳原子的直链或支链烷基基团，优选为甲基基团或三烷基硅基团。M代表金属，优选为周期表的(Ia)族金属，优选为锂。本发明的另一个对象包括通过对先前获得的具有β位置上的光学活性羟基的炔烃进行异构化来生产具有γ位置上的光学活性羟基的炔烃。
• [EN] CIS-2,6-DISUBSTITUTED TETRAHYDROPYRAN DERIVATIVES AND PREPARATION METHOD THEREOF<br/>[FR] DÉRIVÉS DE TÉTRAHYDROPYRANE CIS-2,6-DISUBSTITUÉS ET PROCÉDÉ POUR LES PRÉPARER
  申请人：KOREA INST SCI & TECH

  公开号：WO2009104849A1

  公开（公告）日：2009-08-27

  Disclosed are cis-2,6-disubstituted tetrahydropyran derivatives and a preparation method thereof. The tetrahydropyran derivatives can be prepared by Prins-reacting tetrahydropyran derivatives with homopargylicalcohol derivatives in the presence of trimethylsilyltriflate. The tetrahydropyran derivatives with cis-substituents at both C2 and C6 positions of the tetrahydropyran ring are useful as intermediates for use in the synthesis and development of therapeutically effective, naturally occurring compounds.

  揭示了cis-2,6-二取代四氢吡喃衍生物及其制备方法。这些四氢吡喃衍生物可以通过在三甲基硅三氟乙酸酯存在下，将四氢吡喃衍生物与同炔基醇衍生物进行普林斯反应来制备。在四氢吡喃环的C2和C6位置都有顺式取代基的四氢吡喃衍生物，可作为合成和开发具有治疗效果的天然化合物的中间体。
• CIS-2, 6-DISUBSTITUTED TETRAHYDROPYRAN DERIVATIVES AND PREPARATION METHOD THEREOF
  申请人：CHO Yong Seo

  公开号：US20090209770A1

  公开（公告）日：2009-08-20

  Disclosed are cis-2,6-disubstituted tetrahydropyran derivatives represented by Chemical Formula 1 and a preparation method thereof. The tetrahydropyran derivatives can be prepared by Prins-reacting tetrahydropyran derivatives with homopargylicalcohol derivatives in the presence of trimethylsilyltriflate. The tetrahydropyran derivatives with cis-substituents at both C2 and C6 positions of the tetrahydropyran ring are useful as intermediates for use in the synthesis and development of therapeutically effective, naturally occurring compounds. (wherein, R 1 , R 2 and R 3 are as defined in the specification.)

  本发明涉及一种化学式1所示的顺式2,6-二取代四氢吡喃衍生物及其制备方法。该四氢吡喃衍生物可以通过在三甲基硅基三氟甲烷的存在下，用同型异炔醇衍生物对四氢吡喃衍生物进行普林斯反应制备得到。在四氢吡喃环的C2和C6位置均带有顺式取代基的四氢吡喃衍生物可用作中间体，用于合成和开发治疗有效的天然化合物。（其中，R1、R2和R3如说明书中所定义。）
• Hydrogenation Promoter, Hydrogenation Catalyst, and Process for Producing Alkene Compound
  申请人：Hori Junichi

  公开号：US20080033221A1

  公开（公告）日：2008-02-07

  A hydrogenation promoter of the present invention is produced by reacting an alkyne compound or an alkene compound, a palladium compound represented by a general formula Pd(II)X j L k (where L represents a monodentate ligand or a polydendate ligand other than a phosphorus-containing ligand (when two or more Ls are present in the compound, the Ls may be the same or different), X represents an anionic group, j represents a value determined according to the valence of X so that X j has a valence of −2 as a whole, and k represents an integer in the range of 0 to 4), and a base in an organic solvent. Specifically, The hydrogenation promoter of the invention includes palladium nanoparticles containing the alkyne compound or the alkene compound as an agglomeration-preventing agent.

  本发明的氢化促进剂是通过在有机溶剂中反应炔烃化合物或烯烃化合物、由一般式Pd(II)XjLk表示的钯化合物(其中L表示单齿配体或不含磷的多齿配体（当化合物中存在两个或两个以上的L时，L可以相同也可以不同），X表示阴离子基团，j表示根据X的价确定的值，使Xj整体价为-2，k表示0到4之间的整数)，以及碱的反应产生的。具体来说，本发明的氢化促进剂包括含有炔烃化合物或烯烃化合物作为凝聚抑制剂的钯纳米粒子。
• Cis-2, 6-disubstituted tetrahydropyran derivatives and preparation method thereof
  申请人：Korea Institute of Science and Technology

  公开号：US08115019B2

  公开（公告）日：2012-02-14

  Disclosed are cis-2,6-disubstituted tetrahydropyran derivatives represented by Chemical Formula 1 and a preparation method thereof. The tetrahydropyran derivatives can be prepared by Prins-reacting tetrahydropyran derivatives with homopargylicalcohol derivatives in the presence of trimethylsilyltriflate. The tetrahydropyran derivatives with cis-substituents at both C2 and C6 positions of the tetrahydropyran ring are useful as intermediates for use in the synthesis and development of therapeutically effective, naturally occurring compounds. (wherein, R1, R2 and R3 are as defined in the specification.).

  本发明涉及一种化学式1所表示的顺式2,6-二取代四氢吡喃衍生物及其制备方法。该四氢吡喃衍生物可以通过在三甲基硅基三氟甲烷的存在下，将四氢吡喃衍生物与同型异炔醇衍生物进行普林斯反应制备而得。在四氢吡喃环的C2和C6位置均具有顺式取代基的四氢吡喃衍生物，可作为中间体用于合成和开发具有治疗效果的天然化合物。（其中，R1、R2和R3如规范中所定义。）