1,1,1-Trichlor-2-hydroxy-4-hexanon | 24298-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1-Trichlor-2-hydroxy-4-hexanon
• 英文别名: 1,1,1-Trichlor-2-hydroxy-hexanon-(4)；1,1,1-Trichlor-4-oxo-hexan-2-ol；6.6.6-Trichlorhexan-5-ol-3-on；6,6,6-trichloro-5-hydroxy-hexan-3-one；6,6,6-Trichlor-5-hydroxy-hexan-3-on；6.6.6-Trichlor-hexanol-(5)-on-(3)；6,6,6-Trichloro-5-hydroxyhexan-3-one；6,6,6-trichloro-5-hydroxyhexan-3-one
• CAS: 24298-54-2
• 化学式: C₆H₉Cl₃O₂
• 分子量: 219.495
• InChiKey: SQACEZOTRMIIJX-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  288.3±40.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  1,1,1-Trichlor-2-hydroxy-4-hexanon 在 氢氧化钾 作用下， 生成 (E)-4-oxohex-2-enoic acid
  参考文献：
  名称：

  Random Packs and Their Use in Modeling Heterogeneous Solid Propellant Combustion

  摘要：

  It is shown that random packs of spheres of various sizes can be constructed that model ammonium-perchloratein-binder propellants in the sense that both the size distributions and the packing fractions of industrial propellant packs can be matched, Strategies for dealing with fractional numbers of large particles are addressed, as are strategies for dealing with a large number of very fine particles (fine powder), Fine powder is necessary in a three-dimensional pack to achieve the required stoichiometric ratio of ammonium perchlorate to fuel binder, but is not necessary in a two-dimensional (disk) pack, Some preliminary calculations of the two-dimensional combustion field supported by a disk pack are presented, in which full coupling between the gas phase, the condensed phase, and the retreating nonplanar propellant surface is accounted for.

  DOI：

  10.2514/2.5820
• 作为产物：
  描述：

  水合氯醛 、 丁酮 在 sodium acetate 、 乙酸酐 作用下， 生成 1,1,1-Trichlor-2-hydroxy-4-hexanon
  参考文献：
  名称：

  醋酸酐中的氯醛-酮缩合。氯醛与丁酮、3-戊酮、环己酮和 4-甲基-2-戊酮的反应

  摘要：

  在乙酸钠作为催化剂存在下，水合氯醛在乙酸酐为溶剂中与脂肪族和脂环族酮发生混合醛醇缩合反应。与之前的文献报道相反，丁酮羰基 α 位的甲基和亚甲基均发生反应，得到 1,1,1-三氯-2-羟基-4-己酮的混合物 (1)和 1,1,1-三氯-2-羟基-3-甲基-4-戊酮（2a 和 2b，非对映异构体）。3-戊酮、环己酮和 4-甲基-2-戊酮产 1,1,1-三氯-2-羟基-3-甲基-4-己酮（3a 和 3b，非对映异构体），2-（1-羟基-2， 2,2-三氯乙基-) 环己酮（4a 和 4b，非对映异构体）和 1,1,1-三氯-2-羟基-6-甲基-4-庚酮（5）分别。化合物 5 是由水合氯醛和 4-甲基-2-戊酮形成的唯一产物，因为对亚甲基的攻击受到空间位阻。低熔点非对映异构体 2a、3a 和 4a 之前没有被表征，表现出强大的分子内氢键...

  DOI：

  10.1139/v69-327

文献信息

• Orientation in the Crossed Aldol Condensation of Chloral with Unsymmetrical Aliphatic Ketones
  作者：Eberhard Kiehlmann、Pui-Wah Loo

  DOI：10.1139/v71-260

  日期：1971.5.15

  in the crossed aldol condensation with chloral has been studied in glacial acetic acid and in dimethoxyethane. The reaction is irreversible and not accompanied by dehydration of the resulting 1,1,1-trichloro-3-hydroxy-4-alkanones. Except for butanone, condensation occurs preferentially at the least-hindered position of an unsymmetrical ketone. The α-methyl/α-methylene condensation product ratio obtained

  在冰醋酸和二甲氧基乙烷中研究了一系列 14 种脂肪族酮在与氯醛的交叉羟醛缩合反应中的反应性。该反应是不可逆的，并且不伴随所得 1,1,1-三氯-3-羟基-4-烷酮的脱水。除丁酮外，缩合优先发生在不对称酮的受阻最少的位置。当使用乙酸钠作为催化剂时，由通式 RCH2COCH3 的酮得到的 α-甲基/α-亚甲基缩合产物比率在乙酸中高于在二甲氧基乙烷中作为溶剂。甲基烷基酮烷基的空间大小和链长对 α-甲基对氯醛的反应性有显着影响。
• Synthesis and Novel Rearrangement of 1,1,1-Trichloro-2-alken-4-ones
  作者：Eberhard Kiehlmann、Pui-Wah Loo、B. C. Menon、Nora McGillivray

  DOI：10.1139/v71-495

  日期：1971.9.15

  Strong mineral acids convert 1,1,1-trichloro-2-hydroxy-4-alkanones to 1,1,1-trichloro-2-aIken-4-ones and 1,1,5-trichloro-1-alken-4-ones via an intramolecular chlorine shift from C-1 to −5 of an enol allylic system. Alternatively, 1,1,1-trichloro-2-alken-4-ones may be synthesized from 1,1,1-trichloro-2-hydroxy-4-alkanones by acetylation and elimination of acetic acid or by nucleophilic substitution with thionyl chloride followed by dehydrohalogenation. The two diastereomeric 1,1,1-trichloro-2-hydroxy-3-methyl-4-hexanones do not epimerize during acetylation, and the erythro-acetate resists elimination of acetic acid. Pyrolysis of 2-(1-hydroxy-2,2,2-trichloroethyl-)cyclohexanone yields 2-(2,2-dichlorovinyl)-2-cyclohexenone while treatment of 1,1,1,7,7,7-hexachloro-2,6-dihydroxy-4-heptanone with strong acid leads to the formation of 1,1,1,7,7,7-hexachloro-2,5-heptadien-4-one.

  强烈的矿酸将1,1,1-三氯-2-羟基-4-烷酮转化为1,1,1-三氯-2-烯-4-酮和1,1,5-三氯-1-烯-4-酮，通过在烯醇联烯系统的C-1到-5之间进行分子内氯移位。另外，1,1,1-三氯-2-烯-4-酮可以由1,1,1-三氯-2-羟基-4-烷酮经过乙酰化和消除乙酸，或者通过硫酰氯的亲核取代后脱卤生成。两个立体异构的1,1,1-三氯-2-羟基-3-甲基-4-己酮在乙酰化过程中不会发生对映异构化，而且齐式醋酸酯抵抗乙酸的消除。2-(1-羟基-2,2,2-三氯乙基)-环己酮的热解产生2-(2,2-二氯乙烯基)-2-环己烯酮，而1,1,1,7,7,7-六氯-2,6-二羟基-4-庚酮经强酸处理生成1,1,1,7,7,7-六氯-2,5-庚二烯-4-酮。
• US3991202A
  申请人：——

  公开号：US3991202A

  公开（公告）日：1976-11-09
• Chloral–ketone condensations in acetic anhydride. Reaction of chloral with butanone, 3-pentanone, cyclohexanone, and 4-methyl-2-pentanone
  作者：Eberhard Kiehlmann、Pui-Wah Loo

  DOI：10.1139/v69-327

  日期：1969.6.1

  In the presence of sodium acetate as catalyst, chloral hydrate undergoes a mixed aldol condensation with aliphatic and alicyclic ketones in acetic anhydride as solvent. Contrary to previous literature reports, reaction occurs at both the methyl and the methylene group in α-position to the carbonyl group of butanone, to give a mixture of 1,1,1-trichloro-2-hydroxy-4-hexanone (1) and 1,1,1-trichloro-

  在乙酸钠作为催化剂存在下，水合氯醛在乙酸酐为溶剂中与脂肪族和脂环族酮发生混合醛醇缩合反应。与之前的文献报道相反，丁酮羰基 α 位的甲基和亚甲基均发生反应，得到 1,1,1-三氯-2-羟基-4-己酮的混合物 (1)和 1,1,1-三氯-2-羟基-3-甲基-4-戊酮（2a 和 2b，非对映异构体）。3-戊酮、环己酮和 4-甲基-2-戊酮产 1,1,1-三氯-2-羟基-3-甲基-4-己酮（3a 和 3b，非对映异构体），2-（1-羟基-2， 2,2-三氯乙基-) 环己酮（4a 和 4b，非对映异构体）和 1,1,1-三氯-2-羟基-6-甲基-4-庚酮（5）分别。化合物 5 是由水合氯醛和 4-甲基-2-戊酮形成的唯一产物，因为对亚甲基的攻击受到空间位阻。低熔点非对映异构体 2a、3a 和 4a 之前没有被表征，表现出强大的分子内氢键...
• Random Packs and Their Use in Modeling Heterogeneous Solid Propellant Combustion
  作者：S. Kochevets、J. Buckmaster、T. L. Jackson、A. Hegab

  DOI：10.2514/2.5820

  日期：2001.7

  It is shown that random packs of spheres of various sizes can be constructed that model ammonium-perchloratein-binder propellants in the sense that both the size distributions and the packing fractions of industrial propellant packs can be matched, Strategies for dealing with fractional numbers of large particles are addressed, as are strategies for dealing with a large number of very fine particles (fine powder), Fine powder is necessary in a three-dimensional pack to achieve the required stoichiometric ratio of ammonium perchlorate to fuel binder, but is not necessary in a two-dimensional (disk) pack, Some preliminary calculations of the two-dimensional combustion field supported by a disk pack are presented, in which full coupling between the gas phase, the condensed phase, and the retreating nonplanar propellant surface is accounted for.