3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-en-4-yn-1-ol | 74976-66-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-en-4-yn-1-ol
• 英文别名: 3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-en-4-in-1-ol；5-(2,6,6-trimethyl-1-cyclohexenyl)-3-methyl-2-penten-4-yn-1-ol；(E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)pent-2-en-4-yn-1-ol
• CAS: 74976-66-2
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: ZLYHUMYLMVEHBD-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-en-4-yn-1-ol 在 Ra-Ni 盐酸 、 氢气 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 9-cis-Retinol Acetate
  参考文献：
  名称：

  Preparation of (7Z) - and (7Z,11Z) - vitamin A

  摘要：

  An efficient access to (7Z)- and (7Z,11Z)-vitamin A is described. Following the addition of a C6-acetylenic building block to 2,6,6-trimethylcyclohexanone (2), dehydration of the tert. alcohol 3 and formation of the C15-Wittig salt, the (7Z)-geometry was introduced by partial hydrogenation of the triple bond over Raney-nickel. Following Wittig reaction with (E)-2-methyl-4-acetoxy-2-butenal gave a mixture of the title compounds 8 and 9 which could easily be separated.

  DOI：

  10.1016/s0040-4039(00)79878-9
• 作为产物：
  描述：

  2,2,6-三甲基环己酮 在 正丁基锂 、 硫酸 作用下， 生成 3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-en-4-yn-1-ol
  参考文献：
  名称：

  Preparation of (7Z) - and (7Z,11Z) - vitamin A

  摘要：

  An efficient access to (7Z)- and (7Z,11Z)-vitamin A is described. Following the addition of a C6-acetylenic building block to 2,6,6-trimethylcyclohexanone (2), dehydration of the tert. alcohol 3 and formation of the C15-Wittig salt, the (7Z)-geometry was introduced by partial hydrogenation of the triple bond over Raney-nickel. Following Wittig reaction with (E)-2-methyl-4-acetoxy-2-butenal gave a mixture of the title compounds 8 and 9 which could easily be separated.

  DOI：

  10.1016/s0040-4039(00)79878-9

文献信息

• Palladium-Catalyzed Additions of Terminal Alkynes to Acceptor Alkynes
  作者：Barry M. Trost、Mark T. Sorum、Chuen Chan、Gerd Rühter

  DOI：10.1021/ja9624937

  日期：1997.1.1

  The development of addition reactions wherein the product is the simple sum of the reactants plus anything else (only needed catalytically) constitutes an important goal for enhanced synthetic efficiency. The C−H bond of terminal alkynes (the donor alkynes) can be added to either terminal alkynes (self-coupling) or activated internal alkynes (cross-coupling) (the acceptor alkynes) in the presence of

  加成反应的发展，其中产物是反应物加上任何其他东西（仅需要催化）的简单总和，构成了提高合成效率的重要目标。在催化量的乙酸钯存在下，末端炔烃（供体炔烃）的 CH 键可以添加到末端炔烃（自偶联）或活化的内部炔烃（交叉偶联）（受体炔烃）上。富电子空间位阻配体，三（2,6-二甲氧基苯基）膦。用于交叉偶联的活化内部炔烃（受体炔烃）包括带有酯、砜和酮的炔烃。自偶联完全被交叉偶联所淹没，即使供体和受体炔烃的比例为 1:1。该反应对游离的甲醛、醇、
• Iterative Pd catalyzed additions for a synthesis of methyl 7,8,11,12 tetradehydroretionate
  作者：Barry M. Trost、Arthur E. Harms

  DOI：10.1016/0040-4039(96)00726-5

  日期：1996.6

  A 6 step synthesis of the title compound derives from a palladium catalyzed addition of terminal alkynes to acceptor alkynes.

  标题化合物的6步合成来自于钯催化的末端炔烃向受体炔烃的加成。
• Substituted alkynes useful as intermediates in the synthesis of
  申请人：Hoffmann-La Roche Inc.

  公开号：US04661641A1

  公开（公告）日：1987-04-28

  Compounds of the formula ##STR1## wherein n is either 0 or 1; R.sup.1 and R.sup.2 is hydrogen and the other is hydrogen, hydroxy, oxo group, a protected hydroxy or protected oxo group; R.sup.3 is hydroxy oxo group, .dbd.CH--CH.sub.2 --OH, .dbd.CH--CHO or one of the foregoing groups where the hydroxy or oxo functions are protected; R.sup.4 is --CO--OR.sup.6, --CO--R.sup.6, --CO--NR.sup.6 R.sup.7, --CO--Cl or --SO.sub.2 --R.sup.6 ; R.sup.6 is saturated or aromatic hydrocarbon; and R.sup.7 is saturated or aromatic hydrocarbon or hydrogen, are converted by cleavage of R.sup.4 OH into corresponding cycloalkenes and protecting groups, if present, are hydrolyzed. The compounds obtained are valuable intermediates in carotenoid syntheses.

  化合物的公式为##STR1##其中n为0或1；R.sup.1和R.sup.2是氢，另一个是氢，羟基，氧羰基，受保护的羟基或受保护的氧羰基；R.sup.3是羟基氧羰基，.dbd.CH--CH.sub.2 --OH，.dbd.CH--CHO或上述其中一个群，其中羟基或氧羰功能被保护；R.sup.4是--CO--OR.sup.6，--CO--R.sup.6，--CO--NR.sup.6 R.sup.7，--CO--Cl或--SO.sub.2 --R.sup.6；R.sup.6是饱和或芳香烃；R.sup.7是饱和或芳香烃或氢，通过裂解R.sup.4 OH转化为相应的环烯烃，并且如有保护基，将其水解。获得的化合物是类胡萝卜素合成中有价值的中间体。
• Inhoffen; Erdmann, Justus Liebigs Annalen der Chemie, 1955, vol. 598, p. 51,62
  作者：Inhoffen、Erdmann

  DOI：——

  日期：——
• US4661641A
  申请人：——

  公开号：US4661641A

  公开（公告）日：1987-04-28