3,3-dimethyl-5-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-pent-4-en-2-one | 163715-81-9

• 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: 3,3-dimethyl-5-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-pent-4-en-2-one
• 英文别名: 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-one；(-)-(E)-3,3-Dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-one；(e)-3,3-Dimethyl-5-(2,2,3-trimethylcyclopent-3-enyl)pent-4-en-2-one；(E)-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-one
• CAS: 163715-81-9
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: XOLMHMBQANBLAK-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3,3-dimethyl-5-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-pent-4-en-2-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以95%的产率得到Polysantol (R)
  参考文献：
  名称：

  Synthesis of Polysantol® and related sandalwood-type odorants using magnesium α-bromoketone enolates

  摘要：

  The syntheses of the commercial sandalwood-type odorant Polysantol((R)) and several structurally related compounds are described. The methodology followed is based on a selective and efficient magnesium-mediated aldol reaction of the starting material, alpha-campholenic aldehyde and different alpha-bromoketones. Dehydration of the resulting secondary alcohol and reduction of the carbonyl group allowed the completion of the syntheses of the target molecules in 30-56% overall yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.142
• 作为产物：
  描述：

  3-溴-3-甲基-2-丁酮 在 吡啶 、 magnesium 、 甲基磺酰氯 作用下， 以 乙醚 为溶剂， 反应 1.17h， 生成 3,3-dimethyl-5-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-pent-4-en-2-one
  参考文献：
  名称：

  Synthesis of Polysantol® and related sandalwood-type odorants using magnesium α-bromoketone enolates

  摘要：

  The syntheses of the commercial sandalwood-type odorant Polysantol((R)) and several structurally related compounds are described. The methodology followed is based on a selective and efficient magnesium-mediated aldol reaction of the starting material, alpha-campholenic aldehyde and different alpha-bromoketones. Dehydration of the resulting secondary alcohol and reduction of the carbonyl group allowed the completion of the syntheses of the target molecules in 30-56% overall yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.142

文献信息

• SELECTIVE HYDROGENATION OF ALDEHYDE WITH RU/BIDENTATE LIGANDS COMPLEXES
  申请人：FIRMENICH SA

  公开号：US20140243526A1

  公开（公告）日：2014-08-28

  The present invention relates to processes for the reduction by hydrogenation, using molecular H 2 , of a C 5 -C 20 substrate containing one or two aldehydes functional groups into the corresponding alcohol or diol, characterized in that said process is carried out in the presence of —at least one catalyst or pre-catalyst in the form of a ruthenium complex having a coordination sphere of the N 2 P 2 O 2 , wherein the coordinating atoms N 2 are provided by a first bidentate ligand, the coordinating atoms P 2 are provided by a second bidentate ligand and the coordinating atoms O 2 are provided by two non-linear carboxylate ligands; and —optionally of an acidic additive.

  本发明涉及利用分子H2对含有一个或两个醛基官能团的C5-C20底物进行加氢还原的过程，将其转化为相应的醇或二醇，其特征在于所述过程在以下条件下进行：—至少一种催化剂或前驱体存在，其形式为具有N2P2O2配位球的钌配合物，其中配位原子N2由第一双齿配体提供，配位原子P2由第二双齿配体提供，配位原子O2由两个非线性羧酸盐配体提供；和—可选地加入酸性添加剂。
• Catalytic hydrogenation processes
  申请人：Rautenstrauch Valentin

  公开号：US20050245748A9

  公开（公告）日：2005-11-03

  The catalysts of formula (II): [Ru(L) m (L′) w XY], wherein X and Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, m is 1 or 2, w is 1 when m is 1 and w is 0 when m is 2, L is a phosphino-amine or phosphino-imine bidentate ligand and L′ a diphosphine, are useful for the hydrogenation of substrates having a carbon-hetero atom double bond.

  式子（II）的催化剂：[Ru（L）m（L'）wXY]，其中X和Y同时或独立地表示氢原子或卤素原子，羟基，或烷氧基，羧基或其他阴离子基团，m为1或2，当m为1时，w为1，当m为2时，w为0，L为膦胺或膦亚胺双齿配体，L'为双膦配体，适用于具有碳-杂原子双键的底物的加氢反应。
• [EN] REDUCTION BY A SILANE IN THE PRESENCE OF ZINC CATALYST<br/>[FR] RÉDUCTION PAR SILANE EN PRÉSENCE D'UN CATALYSEUR AU ZINC
  申请人：FIRMENICH & CIE

  公开号：WO2022112118A1

  公开（公告）日：2022-06-02

  The present invention relates to the field of organic synthesis. More specifically, it concerns a process for the selective reduction of a C3-C70substrate containing one or more carbonyl or carboxylic functional groups into the corresponding 5 alcohol diol, or polyalcohol in the presence of a silane and at least one catalyst or pre-catalyst in the form of a zinc complex. The Zinc complex of formula (I) or (II) is also part of the invention.

  本发明涉及有机合成领域。更具体地说，它涉及一种在硅烷和至少一种催化剂或前催化剂的存在下，对含有一个或多个羰基或羧基官能团的C3-C70底物进行选择性还原，制得相应的5醇二醇或多元醇的方法。式（I）或（II）的锌配合物也属于本发明。
• [EN] PROCESS FOR THE PREPARATION OF POLYSANTOL-TYPE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS DE TYPE POLYSANTOL
  申请人：FIRMENICH & CIE

  公开号：WO2017207707A1

  公开（公告）日：2017-12-07

  The present invention relates to the field of organic synthesis and more specifically it concerns a novel compound of formula (I) which could be used as a novel intermediate in the process for the preparation of compound of formula (III).

  本发明涉及有机合成领域，更具体地涉及一种新的化合物(I)，其可用作制备化合物(III)的新中间体。
• Dérivés hydroxylés de l'aldéhyde campholénique, leur utilisation à titre d'ingrédients parfumants et composition parfumante les contenant
  申请人：FIRMENICH SA

  公开号：EP0155591A2

  公开（公告）日：1985-09-25

  Les composés de formula dans laquelle: a. R1 = CH3; n=m=1; R2 = CH3; R3 = R4 = H, b. R1 = CH2; n=0; m=1; R2 = CH3; R3 = R4 = H, c. R1 = CH-CH3; n=0; m=1; R2 = CH3; R3 = R4 = H, d. R1 = H; n=m=0; R2 = R4 = CH3; R3 = C2H5, e. R1 = H; n=m=0; R2 = R3 = R4 = CH3, f. R1 = H; n=m=0; R2 = CH3; R3 = C2H5; R4 = H, g. R1 = H; n=m=0; R2 = R3 = CH3; R4 = H, h. R1 = H; n=m=1; R2 = CH3 R3 = C2H5; R4 = H i. R1 = H; n=m=1; R2 = R3 = CH3 ; R4 = H et dans laquelle l'une des lignes pointillées indique une liaison simple carbone-carbone et l'autre une liaison double, ou chacune des deux indique une liaison simple, possèdent des propriétés odorantes de type bois-santalé et, par conséquent, trouvent une utilisation pour la préparation des parfums et produits parfumés.

  式的化合物 其中 a.R1 = CH3; n=m=1; R2 = CH3; R3 = R4 = H、 b.R1 = CH2; n=0; m=1; R2 = CH3; R3 = R4 = H、 c.R1 = CH-CH3；n=0；m=1；R2 = CH3；R3 = R4 = H、 d.R1 = H; n=m=0; R2 = R4 = CH3; R3 = C2H5、 e.R1 = H; n=m=0; R2 = R3 = R4 = CH3、 f.R1 = H; n=m=0; R2 = CH3; R3 = C2H5; R4 = H、 g.R1 = H; n=m=0; R2 = R3 = CH3; R4 = H、 h.R1 = H; n=m=1; R2 = CH3 R3 = C2H5; R4 = H i.R1 = H; n=m=1; R2 = R3 = CH3; R4 = H 其中一条虚线表示碳-碳单键，另一条虚线表示碳-碳单键。 其中一条虚线表示碳-碳单键，另一条虚线表示双键，或者两条虚线都表示单键，具有檀香类型的芳香特性，因此可用于制备香水和香料产品。