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。
• Practical Synthesis of 3-Methylnonane-2,4-dione, an Intense Strawlike and Fruity Flavored Compound
  作者：Yasushi Kato、Yoshifumi Yuasa

  DOI：10.1021/jf0100954

  日期：2001.8.1

  intense strawlike and fruity flavored compound, has been performed by the aldol condensation of n-hexanal and methyl ethyl ketone, followed by oxidation using sodium hypochlorite in the presence of 4-benzoyloxy-2,2,6,6-tetramethylpiperidine-N-oxide in an overall yield of 59%. The purification of 3-methylnonane-2,4-dione with high purity was performed via copper complexes.

  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。
• [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.
• MnO₂ as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
  作者：Rodney A. Fernandes、Gujjula V. Ramakrishna、Venkati Bethi

  DOI：10.1039/d0ob01344g

  日期：——

  PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is

  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。