(5E)-5-dodecaen-2-one | 81953-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5E)-5-dodecaen-2-one
• 英文别名: (E)-5-dodecene-2-one；(E)-dodec-5-en-2-one；(E)-5-dodecen-2-one
• CAS: 81953-05-1
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: DUBFULMQDVINDM-CMDGGOBGSA-N

物化性质

• 沸点：
  256.1±9.0 °C(Predicted)
• 密度：
  0.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5E)-5-dodecaen-2-one 在 sodium hydroxide 、 三乙基硼 、 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 (5Z,12E)-9-oxo-5,12-nonadecadienoic acid
  参考文献：
  名称：

  Synthesis of new secoprostaglandins as inducers of platelet aggregation.

  摘要：

  合成了两系列的8-乙酰基-12-羟基烯二烯酸和14-羟基-9-氧烯二烯酸，这些化合物可以视为11, 12-和8, 12-秒前列腺素E2，并评估了它们对血小板功能的生物活性。每个系列的关键成员，11, 12-和8, 12-秒-11-去羟基前列腺素E2，被发现能够诱导血小板聚集。该效应被前处理的血小板富血浆与前列腺素I2组合抑制，但并未被吲哚美辛抑制。

  DOI：

  10.1248/cpb.30.51
• 作为产物：
  描述：

  1-壬烯-3-醇 在 4-二甲氨基吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 为溶剂， 反应 1.25h， 生成 (5E)-5-dodecaen-2-one
  参考文献：
  名称：

  THE CARROLL REARRANGEMENT: 5-DODECEN-2-ONE

  摘要：

  DOI：

  10.15227/orgsyn.068.0210

文献信息

• Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as Mild and Reproducible Agents for Rhodium-Catalyzed 1,4-Addition Reactions
  作者：Yoshiaki Nakao、Jinshui Chen、Hidekazu Imanaka、Tamejiro Hiyama、Yoshitaka Ichikawa、Wei-Liang Duan、Ryo Shintani、Tamio Hayashi

  DOI：10.1021/ja071969r

  日期：2007.7.1

  achievement of the corresponding enantioselective transformations using the tetraorganosilicon reagents, providing the silicon-based approach to optically active ketones and substituted piperidones that serve as synthetic intermediates of pharmaceuticals. A rhodium alkoxide species is suggested to be responsible for a transmetalation step on the basis of the observed kinetic resolution of a racemic chiral phenylsilane

  稳定且可重复使用的四有机硅试剂、烯基-、芳基-和甲硅烷基[2-(羟甲基)苯基]二甲基硅烷，在温和的铑催化下与 α,β-不饱和羰基受体发生 1,4-加成反应。该反应耐受多种官能团，适用于克级合成。手性二烯配体的使用允许使用四有机硅试剂实现相应的对映选择性转化，为用作药物合成中间体的光学活性酮和取代哌啶酮提供基于硅的方法。根据观察到的对映选择性 1 中的外消旋手性苯基硅烷的动力学分辨率，建议铑醇盐物种负责金属转移步骤，
• Nickel Acetylacetonate-Induced 1,4-Additions of 1-Alkenyl(Disiamyl)Boranes to α,β-Unsaturated Ketones, Esters and Nitriles
  作者：Teiji Yanagi、Hirotomo Sasaki、Akira Suzuki、Norio Miyaura

  DOI：10.1080/00397919608004563

  日期：1996.7

  conjugate addition of 1-alkenyl(disiamyl)boranes to α,β-unsaturated ketones, esters, or nitriles was carried out in the presence of Ni(acac)2 and triethylamine in DMF. The reactions provided γ,δ-unsaturated ketones, esters, and nitriles in high yields while retaining the original configuration of the 1-alkenylboranes. A similar addition reaction of 1-alkenyl(disiamyl)boranes to 1-acetyl-2-vinylcyclopropane

  摘要 在 Ni(acac)2 和三乙胺的 DMF 存在下，进行了 1-烯基（二异戊基）硼烷与 α,β-不饱和酮、酯或腈的共轭加成。该反应以高产率提供了 γ,δ-不饱和酮、酯和腈，同时保留了 1-烯基硼烷的原始构型。1-烯基（二异戊基）硼烷与 1-乙酰基-2-乙烯基环丙烷的类似加成反应产生末端和内部偶联产物，5,8-链二烯-2-on和5-乙烯基-6-链烯-2-on，在某些情况下以高产率具有有利于末端加成产物的高区域选择性。
• Gaining Absolute Control of the Regiochemistry in the Cobalt-Catalyzed 1,4-Hydrovinylation Reaction
  作者：Marion Arndt、Mehmet Dindaroğlu、Hans-Günther Schmalz、Gerhard Hilt

  DOI：10.1021/ol202696n

  日期：2011.12.2

  The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates the corresponding linear product in both excellent yields and regioselectivities. The catalyst system exhibits a high tolerance toward functional groups, and the very mild reaction conditions allow the synthesis of 1,4-dienes without isomerization into conjugated systems.
• Trost, Barry M.; Martinez, Jose A.; Kulawiec, Robert J., Journal of the American Chemical Society, 1993, vol. 115, # 22, p. 10402 - 10403
  作者：Trost, Barry M.、Martinez, Jose A.、Kulawiec, Robert J.、Indolese, Adriano F.

  DOI：——

  日期：——
• COOLING SENSATION AGENT COMPOSITION AND SENSORY STIMULATION AGENT COMPOSITION
  申请人：Ishida Kenya

  公开号：US20110117147A1

  公开（公告）日：2011-05-19

  The invention relates to a cooling sensation agent composition with a prolonged cool sensation effect comprising at least one compound selected from Formula (1) wherein each of A and B is a hydrogen atom or a hydrocarbon group which may have one or more substituents, in which A and B are not hydrogen atoms simultaneously, and the total number of carbon atoms in A and B is in the range of 6 to 18; and Formulae (2) to (4) wherein R1, R2, and R3 each represent a residue of an alcohol selected from 1-menthol, 1-isopulegol, 3-(1-menthoxy)propan-1,2-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol, 2-methyl-3-(1-menthoxy)propan-1,2-diol and para-menthan-3,8-diol), and R4 represents a residue of a branched or straight-chain, cyclic or linear, or saturated or unsaturated alcohol having 6 to 18 carbon atoms that may have one or more aromatic rings that may have a condensed ring and substituent groups such as hydroxyl and ether groups; and R6 represents a hydrocarbon group having 11 to 19 carbon atoms that may be branched and contain one or more unsaturated bonds. The invention also relates to a sensory stimulation agent composition comprising the cooling sensation agent composition; a flavor or fragrance composition, a beverage or food product, a perfume or cosmetic product, a toiletry product, a daily utensil product or grocery, a fiber, a fiber product, a cloth or a medicine comprising the cooling sensation agent composition or the sensory stimulation agent composition; a production method thereof; a cooling processing method of a fiber, fiber product or a cloth, comprising compounding the cooling sensation agent composition or the sensory stimulation agent composition; and new compounds.