3-methyl-4-hydroxy-2-nonanone | 132412-19-2

• 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: 3-methyl-4-hydroxy-2-nonanone
• 英文别名: 4-hydroxy-3-methylnonan-2-one；4-hydroxy-3-methyl-2-nonanone
• CAS: 132412-19-2
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: LXFRNTODHVJPTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  3-methyl-4-hydroxy-2-nonanone 在 potassium bromide sodium chlorite 、 4-hydroxy-TEMPO benzoate 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-甲基-2,4-壬烷二酮
  参考文献：
  名称：

  实用合成3-甲基壬烷-2,4-二酮，一种强烈的稻草状和水果味的化合物。

  摘要：

  实际合成3-甲基壬烷-2,4-二酮是一种强烈的稻草样和水果味的化合物，方法是将正己酮和甲乙酮进行羟醛缩合反应，然后在次氯酸钠存在下使用次氯酸钠进行氧化。 4-苯甲酰氧基-2,2,6,6-四甲基哌啶-N-氧化物，总产率为59％。经由铜配合物进行高纯度的3-甲基壬烷-2,4-二酮的纯化。

  DOI：

  10.1021/jf0100954
• 作为产物：
  描述：

  3-methyl-non-1-en-4-ol 在 manganese(IV) oxide 、 palladium dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 26.0h， 以60%的产率得到3-methyl-4-hydroxy-2-nonanone
  参考文献：
  名称：

  MnO2 在高烯丙醇和末端烯烃的 Wacker 氧化中作为末端氧化剂。

  摘要：

  通过使用 Pd( II ) 催化剂和 MnO 2作为助氧化剂，已经开发了用于将较少探索的高烯丙醇的末端烯烃氧化成 β-羟基甲基酮的高效温和的反应条件。该方法反应条件温和，官能团相容性好，区域选择性和化学选择性高。而我们早期的 PdCl 2 /CrO 3系统/HCl由高烯丙醇产生α，β-不饱和酮，本方法正交提供β-羟基-甲基酮。没有观察到苄基和/或β-羟基的过度氧化或消除。该方法也可以扩展到简单末端烯烃的氧化，以及甲基酮的氧化，显示出其多功能性。展示了姜酚在区域选择性合成中的应用。

  DOI：

  10.1039/d0ob01344g

文献信息

• Catalyst-Controlled Wacker-Type Oxidation of Homoallylic Alcohols in the Absence of Protecting Groups
  作者：Jessica R. McCombs、Brian W. Michel、Matthew S. Sigman

  DOI：10.1021/jo200462a

  日期：2011.5.6

  Homoallylic alcohols are oxidized to β-hydroxy ketones using a TBHP-mediated Pd-catalyzed Wacker-type oxidation. The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP(aq) as the terminal oxidant provides good yields of the desired products with reaction times significantly reduced as compared to the Tsuji−Wacker oxidation. Additionally, bis- and tris-homoallylic alcohols are oxidized

  使用 TBHP 介导的 Pd 催化的瓦克型氧化将高烯丙醇氧化为 β-羟基酮。使用双齿配体、喹啉-2-恶唑啉 (Quinox) 和 TBHP (aq)作为末端氧化剂提供了所需产物的良好收率，与 Tsuji-Wacker 氧化相比，反应时间显着缩短。此外，双-和三-高烯丙醇被氧化以提供环状过氧缩酮，推测是通过甲基酮产物的亲核攻击。
• Fragrance and flavor compositions and fragrance- and flavor-added products
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20030092599A1

  公开（公告）日：2003-05-15

  Ketone compounds having marine-like, modern green-like and fatty green-like fragrance and flavor, and fragrance compositions and flavor compositions containing the same. A fragrance or flavor composition which contains one or more of ketone compounds represented by the following general formula (1) 1 (wherein A is C═O or CH—OH, R 1 is hydrogen atom or methyl group and R 2 is methyl group or ethyl group, with the proviso that R 2 is ethyl group when R 1 is hydrogen atom, and R 2 is methyl group when R 1 is methyl group) as the aromatic component.

  具有海洋般、现代绿色般和脂肪绿色般的香味和味道的酮类化合物，以及含有这些化合物的香味和味道组合物。其中一种香味或味道组合物包含下述一般式（1）所代表的一个或多个酮类化合物（其中A为C═O或CH—OH，R1为氢原子或甲基基团，R2为甲基基团或乙基基团，但当R1为氢原子时，R2为乙基基团，当R1为甲基基团时，R2为甲基基团），作为芳香成分。
• New Oxidation of β-Hydroxy α-Methyl Ketones:  A Convenient Synthesis of 3-Methylalkane-2,4-diones
  作者：Yoshifumi Yuasa、Yasushi Kato

  DOI：10.1021/op020029i

  日期：2002.9.1

  The synthesis of 3-methylalkane-2,4-diones, which are intense strawlike and fruit-flavored compounds, has been performed by the aldol condensation of n-alkanal (C2-C7) and methyl ethyl ketone to give 4-hydroxy-3-methyl-2-alkanones in 31-72% yield, followed by oxidation using sodium hypochlorite in the presence of 4-benzoyloxy-2,2,6,6-tetramethyl-piperidine-N-oxide in 60-86% yield.
• [EN] COOLING SENSATION AGENT COMPOSITION AND SENSORY STIMULATION AGENT COMPOSITION<br/>[FR] COMPOSITION D'AGENT DE SENSATION DE FRAÎCHEUR ET COMPOSITION D'AGENT DE STIMULATION SENSORIELLE
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2009123355A2

  公开（公告）日：2009-10-08

  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 l-menthol, l-isopulegol, 3-(l-menthoxy)propan-1,2-diol, 2-(l-menthoxy)ethan-1-ol, 3-(l-menthoxy)propan-1-ol, 2-methyl-3-(l-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.