4-hydroxy-6,10-dimethylundec-9-en-2-one | 33027-94-0

• 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: 4-hydroxy-6,10-dimethylundec-9-en-2-one
• CAS: 33027-94-0
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: WHZCZPLQNCFJSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6,10-dimethylundec-9-en-2-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 mercury(II) diacetate 、 对甲苯磺酸 、 sodium sulfate 作用下， 以 乙醚 、 苯 为溶剂， 反应 30.0h， 生成 S-(+)-11-methoxy-3,7,11-trimethyldodecadienoic acid isopropyl ester
  参考文献：
  名称：

  Synthesis ofS-(+)-methoprene

  摘要：

  An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. approximately 50%) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol. This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5). Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one. The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14% overall yield.

  DOI：

  10.1007/bf00699984
• 作为产物：
  描述：

  6,10-dimethylundeca-1,9-dien-4-ol 在 copper(l) chloride 、 palladium dichloride 氧气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-hydroxy-6,10-dimethylundec-9-en-2-one
  参考文献：
  名称：

  Synthesis ofS-(+)-methoprene

  摘要：

  An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. approximately 50%) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol. This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5). Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one. The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14% overall yield.

  DOI：

  10.1007/bf00699984

文献信息

• Ti-Catalyzed Reformatsky-Type Coupling between α-Halo Ketones and Aldehydes
  作者：Rosa E. Estévez、Miguel Paradas、Alba Millán、Tania Jiménez、Rafael Robles、Juan M. Cuerva、J. Enrique Oltra

  DOI：10.1021/jo702189k

  日期：2008.2.1

  We describe the first Ti-catalyzed Reformatsky-type coupling between α-halo ketones and aldehydes. The reaction affords β-hydroxy ketones under mild, neutral conditions compatible with ketones and other electrophiles. The catalytic cycle possibly proceeds via bis(cyclopentadienyl)titanium enolates.

  我们描述了α-卤代酮和醛之间的第一个钛催化的Reformatsky型偶联。该反应在与酮和其他亲电子试剂相容的温和，中性条件下产生β-羟基酮。催化循环可能通过双（环戊二烯基）钛烯醇化物进行。
• Total Synthesis of an Antifouling Marine Furanosesquiterpene
  作者：S. Murphree、Chad Ungarean、Jeremy Mason、Benjamin Eyer、Nicholas Duca、Jaimie Mong

  DOI：10.1055/s-0036-1588711

  日期：——

  Abstract An antifouling sesquiterpene isolated from Sinularia sp. was synthesized from citronellyl acetate in eight steps and 9% overall yield. The furan moiety was constructed using a multifunctional sulfone reagent. An antifouling sesquiterpene isolated from Sinularia sp. was synthesized from citronellyl acetate in eight steps and 9% overall yield. The furan moiety was constructed using a multifunctional

  摘要 从Sinularia sp。分离的防污倍半萜。由乙酸香茅酯以八步合成，总收率为9％。使用多功能砜试剂构建呋喃部分。 从Sinularia sp。分离的防污倍半萜。由乙酸香茅酯以八步合成，总收率为9％。使用多功能砜试剂构建呋喃部分。
• Breuilles, Pascal; Uguen, Daniel, Bulletin de la Societe Chimique de France, 1988, # 4, p. 705 - 720
  作者：Breuilles, Pascal、Uguen, Daniel

  DOI：——

  日期：——
• Synthesis ofS-(+)-methoprene
  作者：V. N. Odinokov、G. Yu. Ishmuratov、R. Ya. Kharisov、E. P. Serebryakov、G. A. Tolstikov

  DOI：10.1007/bf00699984

  日期：1993.1

  An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. approximately 50%) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol. This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5). Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one. The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14% overall yield.